Bridget Harris: The Buskers Guide to Running a Tech Startup

“Wait a sec… if I DON’T take your money, I will fail. If I DO take your money I will likely fail… what?!”

Bridget is the co-founder and CEO of, a SaaS tool which allows your customers to easily book your time, fuss free. At BoS Conference Europe 2016, she discussed the growth of the company, and likened her busking background to that of her experience of growing a company. She touched on many of her experiences in growing, from dealing to VC’s, to remote working, to the hiring process and their policy of ‘blind hiring’ to ensure the best people get the job based on merit alone, and shared actionable tips on each of these.


Brilliant AMA with Bridget and Peldi discussing Remote Working

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Busking = Bootstrapping, pirate hacking, etc.

#1: Hire Professional Musicians… Busking only takes you so far.
We’ve got no money so we have to think” – Ernest Rutherford, Physicist.
This sums up what being a bootstrapper is about.
If you don’t have money, you make decisions more slowly.
Money doesn’t necessarily make things better or or easier.

VC Insanity

If you don’t take money, you’ll fail.

With VC funds you have to make 10x in 5-7 years to make up for the 90% of business in the fund that fail.
“Why do I have to make up for your bad investment choices?”
Wait a sec… if DON’T take your money, I will fail. If I DO take your money I will likely fail… what?!

Thoughts on VC

“It takes about ten years before your company really hits its stride” – Mailchimp Founder
The strategies employed to pursue 30% for $3m, are often in direct opposition to the strategies needed for a .3% shot at making $300m” – DHH of Basecamp
“Maybe some percentage, larger than 95% of VCs, add zero value, and 70% of VCs add negative value in advising” – Khosla Ventures
There’s no perfect way! It’s OK to have  values that are counter VC!
“Government is the badge of lost innocence” – Thomas Paine, Common Sense, 1776
This feels like in terms of HR you have to have policies and procedures handbook about holidays, expenses, and other boring things… and it’s not necessarily the company I would be ambitious to build.
If I have to be on a ship for 15 years, it will not be a super tanker (big corporate)… it’ll be a cruise ship!

You Can’t Busk Hiring

You need to have an actual [good] STRATEGY for hiring.
“There are only two possible outcomes to this decision: HIRE or NO HIRE” – Joel Spolsky,
If you are really questioning the hire… it’s a no hire.
Most people are NO HIRE (~95)
You want people who are smart AND gets things done!
Smart and NOT GTD = no good
GTD and not smart = lots of bad / unnecessary things get done well.

Assumptions on challenges for hiring… WERE WRONG

We were not in London and everything that matters is in London
We have to compete with the insanity of SHOW ME THE MONEY developers in the tech space.
Who are we? No one knows who we are and would not want to work with us.
Most of our users were… NOT FROM BEDFORD. HAHA.
We invested in branding and content about our culture and team… this solved the problem of generating interest in wanting to work with us!

Remote Company

This isn’t a cheapskate move… it’s a different strategy!
We are willing to invest in the hassle. We are trying to build a real company that grows and invest appropriately
We definitely value face-to-face engagement.


Hire people an order of magnitude smarter and better than you!

Check your ego at the door! You are trying to build a team and spread the load.
Pay the most you can for the most talented people you can.
if you try to hire junior people, you spend all your time managing them.
Make it VERY CLEAR you value remote work.

We want people who want an actual full professional career as a remote worker.

Stage ONE: We say NO when… (don’t bother with these people)

Anyone that says “to whom it may concern”… I know you don’t fit.
It concerns me!
Generic form letters
… you know… those people who obviously won’t work

Stage TWO: Detailed Questionnaire.

We tend to keep a control group of internal people that have not seen any previous information about the people regardless of background, rate, etc
People that include information that is absolutely irrelevant to me.
Really unfortunate and obvoius tpyo (see what I did there)
People that don’t like or live tech
Anyone that denigrates their opponents to promote themselves.
When you see this behavior you are looking at someone who looks at RELATIVE, not objective talent and quality.
People that are weird about money and think money is a main driver in the company.
We are open and transparent about salaries and the reality that we are bootstrapped.
We follow up on references!

Stage THREE: The Video Call

At this point, it starts to speed up. You don’t want half of your company sitting around a laptop when it is an obvious no-hire.
This is a 20min call.

At every stage we are looking for REASONS NOT TO HIRE them.

A wrong hire is a TERRIBLE MISTAKE.

If Not them… then who?

At some point you have to take the leap to actually hire…

Stage FOUR – The Contract

A 3 month contract to gauge actual fit.


Experiences vs. Bright…

The only downside to being a remote company is it is very hard to hire unior people remotely because they do deserve more support and training… which is a very scarce resource for us .
It kind of depends on the mindset of the company.
I have primarily focused on senior level managers who can hire down as we grow and scale. This also helps people have greater autonomy and motivation for the future.
We need people who are willing to do whatever is necessary.l

What are other key challenges of remote working…

Communication, project management, collaboration have to be very intentional.
You have to be part of a virtual social online thing.
Right now we are only 12, so as we grow it will be more difficult.
No email because it is is annoying.
Email removes transparency. Everything is discussed in Hipchat.

Before hiring full time… did you go through a period of freelancers? How was that? When did you transition to hire vs. freelancer.

It depends on the demands of the business. E.g. We should have hired full time support sooner.
We should have hired earlier in a much more confident way.
I want people to be part of the growth… freelancers hedge their bets by never committing.
I try to very intentionally control the process.
We want people who work just as hard to find us.

Curious about the blind hiring process? Do you use any specific tools

I removed all personal information from answers so they could see ONLY the answers of everyone side-by-side.
I think this helps with diversity because it removes unconscious favorites.
The two hiring managers also switch off on the blind process… even to through the video call.
We track applications by mobile phone number, not even name.
Use an actual system with a funnel instead of email + attachments.
You are kidding yourself if you think you don’t have biases or favorites.

How do you handle payroll across different countries?

In the USA, our lawyers first advised us to get an agency to do it all for us…. i didn’t go this route because I wanted youcanbookme to be on the stub.
We have an accountant in the country that helps us.
State legislation is a nightmare.
Zenpayroll … now Gusto.
It’s is almost impossible to get health insurance for people in different states.
Europe hiring is hilarious can take months…
Spain is crazy, everything has to be double translated, stamped on every page, and full of bureaucratic insanity…
Ireland is took half a day to setup because there is such little red tape.

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Bridget Harris: Thank you! Good morning everybody! As Mark said my name is Bridgette Harris and I’m the co-founder and CEO of is a SaaS tool, we do online scheduling, we’re also freemium so some of the numbers you will hear me talk about, is because we have a large number of free users and a proportion of those guys pays us upgrades. This is actually a couple of months ago. We’re up to around 13 million bookings to date, we do about 1 million bookings a month, the vast majority of people that use us are in North America but we’re spread around the world.

The Busker’s Guide to Running a Tech Start-Up

The title of this talk is ‘The Busker’s Guide to Running a Tech Start-Up’. I’m not sure whether the term busker comes up often when people talk about software businesses but just in case you’re wondering I am actually a busker. That’s me last month on St. Patrick’s day kicking off the celebrations in our local pub. I started busking when I was very young a teenager, looking for an easy way to make money. It’s actually an incredible experience if you put your case down in Victoria Station and start playing and somebody walks by who didn’t know you were gonna be there and stick some money in the case. And I got addicted to it, it was a brilliant way to make money. And that’s I think what I hope you will recognise it feels like to be an entrepreneur. It’s basically the name of the game, it’s about getting people to give you money, people who didn’t know that they needed the product that you’re offering. And so whether it’s a busker or you call yourself an entrepreneur or hustler or disrupter or pirate, even if it’s just a business level, all of this is about taking the risk and the leap to asking people to give you money for what you’re selling and involved in that is a good deal of busking

So at any point and hopefully I will leave plenty of time for questions, but I don’t mind being interrupted for questions along the way, at any point if you think anything I’m saying is not consistent to busking, I will happily explain why. But that element of improvisation, not following the rules, when you’re a session musician you play it by ear, you don’t just simply follow the dots and there’s a lot of enjoyment to it as well so that’s why I love doing it and that’s why I love running a start-up.

The first rule…

But the first rule of being a busker running a start-up is hire professional musicians as quickly as you possibly can because busking can only get you really so far. And one of the things I’ve learned in the last couple of years is once you get a team of professional classical musicians in this kind of organisation, you can get a lot more out of what you’re trying to achieve, busking only takes you so far.

So I want to talk a little bit about the background of so you understand a bit more about the way we’ve grown up as a company and then I want to spend the majority of the talk, talking about hiring. How you get from being a busker to a point where you hire people and we’re now looking at getting to the next stage of our journey and one of the most important things we’ve decided early on and it’s been a lot in the last couple of days and I’m really interested in this topic, is that we’re bootstrapped so we didn’t take VC funding, we decided to go at it alone.

We’ve got no money so we have to think.

This sums of what being bootstrap is about and Rand just talked about it and it’s come up, that if you don’t have a lot of money, you pretend you take decisions more slowly, you have less options and money doesn’t flood the channel and maybe clouds some of the decisions that you’ve got to make anyway. Money doesn’t necessarily make things easier it’s my point.

But the temptation of taking money is there and if you’re like us and we haven’t got any experience of running a tech start-up before, when you come across angel investors and people give you this expectation that taking on investment is part of running a start-up and there is no alternative. And they’re really emphatic about this and say: if you take on angel investing,

  • you will grow quicker;
  • You will make more money and;
  • you’ll access great advice

I’m sure that’s true for a lot of people but also the implication is if you don’t do this, then you will fail. If you don’t do this, you might as well go home because this is the only way. But I find that really hard and I kind of basically was naïve, but I didn’t really understand what they were saying because when you start talking a bit about the detail about the evaluation and the metrics and the math associated with the money they will give you, they will start saying, we need 10 times what we’ve given you in about 5-7 years.

What? What does that mean? That means that we would have to be at hundreds of millions of pounds, what are you talking about? And they said that’s because 90% of the businesses we invest in fail. So hang on, let me get this right! 9 out of 10 businesses you invest in fail? Yes, that’s right. That’s a very high rate of failure amongst start-ups. So I have to make up 10 times more than I would otherwise have to do in order to make up for your bad investment choices? And they’re like no, it doesn’t exactly work like that. I said but then you’re also saying that if I don’t take your money I’m also going to fail. So hang on, this doesn’t make any sense to me, so maybe I just don’t understand it, and we’ll put you to the side and we will carry on. And in fact as we’ve carried on we understood that it isn’t the case for a lot of companies and you will find people who will give you totally different point of views.

Be patient

So this is Ben and he’s the CEO and co-founder of mail chimp. It’s a unicorn tech company, they haven’t got any flies on anybody I think. And he said, it’s a really simple point, and I think we heard it from so many speakers now. It takes about 10 years before your company really hits its stride. So his point is; be patient. The journey that you’re going on isn’t some kind of quick flip and it’s sort of 12 months and you make 100 million and then you go off and do something else.

Actually, we’re in it for the long term and the learning that we put in to our product and customers and running our business takes a long time. The mistakes you make, the things you then understand you should have done differently and the opportunity in time to get that right, that takes a long time and it becomes a very enjoyable process if you realise that is actually the point. And the exit, the thing at the other end, might be nice if that ever comes along but that’s not necessarily the goal for the entrepreneur.

The other company that’s a big hero company of mine is basecamp. I know David has spoken at this conference a couple of times and he’s full on about this topics and he’s great. I’d read his last medium blog post that he was supposed to deliver it at Web Summit this year and it’s just one big rant about VCs. But he says; the strategies used to employ the 30% for $3 million are often in direct opposition to the strategies needed for a 0.3% shot at making $300 million. His point is that the financial motivational and incentives of the angels and LP’s they have to report into, they all scale at what they try to achieve, might be incompatible with your financial planning and they might accidentally damage it and this idea that you’re gonna make money, you will do so for them. You’re not necessarily gonna make more money for you because your financial and business plans might actually be distorted to a point where you end up really at the end of the food chain, in the financials to do with your company.

And then this final point that being and taking on a big slipstream of VC’s. And I must say that Rand has actually proved the opposite that it doesn’t always work out like this. So it’s great that there’s a good example of the alternative. This is Khostler who is himself a VC but he was at Sun Microsystems. He’s another great ranter on stage and great person to listen to. He says maybe some percentage larger than 95% of VC’s add 0 value and 70% of VC’s add negative value in advising. What he’s saying is just don’t listen to them! So even if you do take money, nod and smile. Because and who was it? Nick, yesterday, did exactly that and obviously he was right. So it’s not obvious and I suppose my point is that running a start-up, a company, it will be really hard and you’ve got the hard way and tricky way, but neither way is gonna help you and this is what we have learned in our decision to be bootstrapped, and the way that’s affected many other parts of our company.


So I want to talk one other aspect of our company, before I get on to higher stuff which is cultural, so what sort of company have we built? So this is one of my favourite quotes, ‘government is the badge of lost innocence’. And this is obviously a political quote, Thomas Paine is a theorist but if you want to know how it feels like it’s in terms of HR you have to have a policies and procedures handbook about holiday and expenses and it has to all be written down and there is a thing and it all feels incredibly boring.

And it’s not necessarily the company that I would be ambitious to want to build cause I think where perception is this is what your average corporate company looks like. And so once you get to the IBM scale, you have a very familiar hierarchy of all the teams and departments are in their containers. Everybody is on the ship and knows where they’re supposed to be, the captains at the top and famously with super tankers very hard to turn them around, they only go a certain speed and have no flexibility but at least the chain of command is really obvious to everybody. Everyone knows what’s going on there.

But given the fact we have an opportunity to build our own company, we can do what we like. This is the kind of ship that we want to be on so if I’m gonna have to basically be on this ship for 15 years oh my goodness! I’m certainly not doing the super tanker. So this is what we’re aiming for. People that can get off by helicopter, there’s a lot of walking around, large transparency and openness and trying to understand what the journey feels like and not just the destination. We’re not just going back and forth across the Pacific, we’re trying to enjoy the journey.

So this is our team, we’re 12 people right now, we’re remote team. I will talk a bit about that as well in a second. So this is our team, we’re based around North America and Europe. We have Niamh down here and she’s in Dublin and we’re a very happy bunch. The reason why I got this photograph and this is just a quick shootout for Zoom US in case you’re wondering because it’s the only video tool available to do this job. I made sure that in our company – there’s Keith who is down here, my co-founder – even though we work out of the same office, 3 of us and Claire also commutes in sometimes we all have our own box. Even when I’m sat next to Keith in the same office, I say no, I want my own box. Because my own box means that everybody in our company has their own box and as a remote company, when you’re distributed, you’re sending out signals as part of your culture about what kind of ship you run basically. And to that end the team didn’t want to give us the wrong impression about what team meetings are really like and that’s they sent through shortly after about our meetings.

Hiring is the most important thing you will have to do to grow

So the point about this is how did we get from these guys and a busking beginning through to building a team like this? I suppose you can’t busk hiring, it’s something that we did at the beginning, made quite a few mistakes with. And you know, busking has a great place when you’re trying to hustle and make up something that didn’t exist before. But actually hiring is the most important thing I think everybody has said it in this conference, the most important thing that not just a CEO has to do but also other people that you hire themselves will have to do if you want to grow. If you have taken on money, the money is there to spend it on often hiring people and so to have a good strategy for hiring people, and to know about it and to read about it is something I really recommend you guys do and this is what I did and I’m here to share with you a bit about that.

Hire or no hire

The first place I would go is Joel Spolsky’s gorilla guide to interviewing. It’s a 3-part blog series. He’s also spoken here I think, Mark? So and he puts it – as soon as he talks about it, you think, yes that’s exactly right! He says there are only two possible outcomes to this decision. Hire or no hire. And he says a hire isn’t somebody that oh well they didn’t do very well in the interview but maybe they’re a bit nervous or actually they don’t quite have the experience but maybe we can train them up or they’re not right for our department but they can be good for someone else– they are all no hires! So don’t kid yourself! I think what you’re looking for is hire and 99% of the people you will talk to for your company are gonna be no hires.

The other point he says that’s the sort of person you’re looking for and this again sounds very simple, it smart and gets things done. His argument is you don’t want smart, doesn’t get things done. Everybody knows that person. And then also, worse, gets things done, not smart. Cause a lot of bad things suddenly get done. So smart gets things done. That’s the aim.

And so at the very beginning – again, as a sort of a symptom of being bootstrapped, we were very slow burn as a company and it was just me and Keith for a long time so as we hired, we made a lot of assumptions about what it was gonna feel like when we were a much bigger company. And the first is – this is where we live, in Bedfordshire in the UK – and the first thing that I was afraid of or fearful is that how we’re gonna get people to come and work for us in Bedford? No one has ever heard of Bedford, we’re gonna have to think of some home grown talent inside Bedford because basically there is London and we’re not London. And anybody who is anybody who wants to work for a tech start-up wants to work in London. I had all these theories and plans about that to solve that problem.

Second assumption I made was you see these stories about – this came up quite recently, he managed to get $250k a year from Air BnB – and you’ve got this massive cattle market of tech companies hiring developers and if Seattle is bad, I’m sure Silicon Valley is worse and everybody ratchets it up. Not only that there are these massive tech companies able to pay these huge salaries but also there is the kind of equity share option, hedged invested, long term pooled stuff. And any conversation that we were gonna have with any developer I felt like this is what it’s gonna be like. And oh my god! There’s just no way we’re gonna ever be able to compete and get any of those developers!

My third assumption was a sort of feeling like who would ever believe we were a tech start-up, we knew what we were doing it? It’s like an impostor syndrome at its worst because you sort of – it’s almost like an inverse, you’re grateful for people that want to work for you and if anybody takes you seriously – and we had to get over that because basically we were wrong about all 3 assumptions and we did make mistakes because of those assumptions but thankfully we got over them quite quickly.

And the first one was because of the first developer we hired. His name is Antonio and lives in Spain. Spain is possibly not Bedford and so the first thing Antonio said was: you do know I have no intention of moving to Bedford. I’ve never even heard of it – I live in Seville in Spain. It’s lovely and hot! The food is good! Are you happy with that? And me and Keith were like yeah, of course! Why wouldn’t we? Because you start to follow through on the logic and this is a snapshot of some of our active users from intercom, which is obviously another great tool! And there we are in Bedford, in the UK. I do recommend you come here it’s a very nice place! But all of our users are not from Bedford, they are trying to do online scheduling they don’t care. So like nobody has ever said I’m not gonna use because you’re based in Bedford. Ok, that’s fine.

So in terms of like a map of the world from a perspective, we’re completely global. And actually surely that’s the most exciting opportunity, especially cloud tools offers. It’s just irrelevant. And actually we do need to hire people in the US and we have done because that’s where our users are. So we need to supply the service to the people where they are, nothing to do with where I choose to live.

So and then the final assumption is this idea that nobody would ever want to work with us. That is fairly easily solved. We just invested in some branding and creative promotion. And so this is on our jobs page and we promote the things that we think are important about why we like working for and therefore why somebody else would want to work for us. So we’re flexible, family friendly and have team members all over the world. We care about our impact, we’re a very values lead company and so we do lots of not for profit stuff. And we’re very open about what problems we’re trying to solve and very collaborative. And there’s a great team and what we found is rather than trying to pretend that we’re second class versions of Air BnB the people that have come to work for us actively want to work for a bootstrap company, we’ve given them the opportunity of saying this is the journey, this is our growth and what you can do with it and actually we don’t have VC’s giving us bad advice or indeed giving any kind of advice. We can do what we like and we’ve also got to – we have to forge our own path and that’s the exciting challenge so for some of the engineers, it’s actually the active point that has led them to come to work for us.

And there they are, in Bedford, in one of our face to face meet ups. So anybody talk to me about remote work and building a remote company is something I’m interested in and take a lot of inspiration for companies like Buffer and others but face to face meetups is just as important and you’ve got to invest in it. And there’s no sense that being a remote company is some kind of cheap skate move as far as we’re concerned so we have set up in Ireland, Spain and America to hire guys where these people are employed, they have the protection associated with being employed by us so there’s lot of administrative and legal hassle that we’ve had to work through to get to that point, but it’s because what we believe is that we’re building a company with employees and not just trying to build some sort of skeleton work force to try to proper me and Keith in Bedford. We’ve embraced the fact that we’re remote but then it’s also lovely to have these guys come to Bedford to see us.

So I want to take you through how we hire and how that process looks like. In quite a lot of detail, I will try to skip through it but in a way it’s a little bit like the relentless follow-up emails that were relentless about this and quite committed and it’s worked really well and don’t skip a stage basically.

Hire people smarter than you

So as I said, the point and – that’s me and Keith in our office and it’s just us and you know what that feels like and you’re either there. This was our first little office that we had, we branched out next door as well, but we started in a coffee shop. And you wear 15 hats and I think the first thing that you have to realise when you look to hire people is that you need to hire people smarter than you, better than you. These people need to be of an order better at what you’ve hired them to do than what you are capable of doing cause you’re gonna be crushed if you think that it’s all gonna be down to you.

So this is the tier 1 of our tier meetings. And actually Clare is one of our recent recruits, she is head of operations. When I was interviewing her, she told me that what she loves doing in the weekends is she plays in an orchestra and she’s a flutist. So she’s an actual classical musician! And I said well I’m a busker and her face just looks slightly horrified and I was like I really am a busker! And then I said that’s why I hired you, Clare! Because classical musicians play with all the dots [laughter]. You’re legal and compliant so this is good news that I’m not doing it anymore. So that’s been one of the principles.

You can’t be egotistical about it, you’re not trying to win the award as the best employee of the company, you’re trying to get a team, spread the load and have a very high bar so I would also completely reiterate and agree with some of the speakers and Rand’s just said it, you’ve got much better to pay the most you can for the highest talent and people that you can attract than try to get a lower grade pull where you’re hedging your bets because what I found is if you try to hire junior people you spend all your time managing them so it doesn’t save you any time.

So the advert. Going back to the fact that we were a remote company, we advertise depending on what role we’ve been filling. We obviously go for one of these obvious job boards and all I would say is make it clear for us because we’re remote, we make it very clear in our adverts that we’re remote and that’s who we’re looking for, for people who want to work remote and get – we’re not looking for people who think it’s about working from home so they can do their pottery business on the side, but people who actually want to work for a company as a full time professional job and career with all the things that come with it, but happen to do it from a coffee shop or indeed from their home if they want to.

And then we have this process which is along the general lines of things, which we’re looking for the hires and no hires and it’s very easy because you stop about hires. You don’t think about who will you hire at all, just who you’re not gonna hire, who are the obvious people that are not gonna work on the company. And then the application flood in, it’s really easy. You can exclude about 85% of them. The first is to whom it may concern anybody that sends me a cover letter says to whom it may concern – there’s only 12 of us. You can google me. Honestly! It would take less than a minute to find out – it concerns me! Or me saying to the hiring manager – no, but this is the operations job that includes it. There is no hiring manager, so that’s very bizarre. And also anybody that applies to your company where they have their generic logo, cover letter, CV, they haven’t thought about the job and what they’re doing – this is an example.

This is for our UI-UX job. We’re a SaaS tool and the job was for UI and they say non applicable. So it’s non applicable, what examples they’re inspired by for the job they were replying for? So that’s a no hire. And then the next no hires are just the people obviously the idiots that I don’t think it’s gonna work out, I don’t think this is [laughter] good luck with you! But it’s not gonna work out! So obviously that’s a very easy process. You don’t spend a lot of time on it, it’s super easy cause you will have potential hires in the pack, don’t spend any time reading cover letters when it starts with to whom it may concern it’s a no hire because then what we do is we shorten this and we’ve done this for lots of jobs and we send a google docs form.

This is for JavaScript and this product advisor and customer support person and we take lots of questions about their actual name and address and more details about them, but then we also put in a whole load of questions. So we give them opportunities to talk about things that they’ve done, problems that they’ve solved, how they would handle situations, anything that would give us an opportunity to really understand more about how they could apply the work that we’re asking them to do. And the great advantage of this is you then start to be able to compare and contrast some of those applications and answers and what I’m a big believer in when your applications flood in, what we tend to do is there are always a group of people who are interviewing who haven’t seen the lead up and details of that process to the people who are short listed and vice versa. You can anonymise the data so that spreadsheet comes in, I chop off all of the name, address, their college, where they live, their hourly rate so that you don’t start thinking if they’re 250000 a year or an engineer, they will have to be brilliant. But if she is a $15 Ukrainian, that’s probably not gonna be worth it because you’re subconscious bias, it immediately comes up at an early stage and once you take all of these questions and say the tech team are looking at those answers, they can just compare 5 answers to the same question and they have no idea who wrote the answer! And then they can immediately start to exclude the no hires and this is where we have to put a much deeper analysis of who is our definition of a no hire.

So the first no hire is anybody that includes information about their job which is absolutely irrelevant to their ability to do it. So the other thing which is totally off topic and you think no, you just spent 30 minutes writing out this application for, you should have thought about what kind of company you’re working for and why are you talking to me about it?

The next one is really unfortunate typos – is that awful? So it’s very close to his heart the 7/11. Obviously most tech companies, we’re looking for coders and people who have really got accurate brains and attentions to detail and if you say I’m really good at attention to detail and then you come up with a terrible typo, that’s a no hire.

So yes, we do online scheduling. People have sent us in letters and say I don’t use digital calendars, I just use a good old fashion pen and paper. And you think ok, that’s good! I like that! Good luck with you! But we’re a tech company and you really need to like tech and you don’t need to think I will learn how to like tech if you give me the job. You really do need to like tech.

Anybody that denigrates their opponents as a way of trying to promote themselves. Anybody who talks about their work colleagues and when you put these questions to them in the questionnaires and their stories are all about how they disagreed with somebody else because they got it wrong so they did something better. Even if on objective terms there was some merit to it, I think that when you see that kind of behaviour, what you’re looking at is somebody who is not trying to go for objective talent and quality, but they are going for relative talent and quality. And especially when you’re a remote company, it’s absolutely toxic cause it brings in so much lack of trust in any person or relationship when you think somebody will be slacking off every 2 minutes.

Anybody who is weird about money talks about how much money they’ve earned or in some way tries to think that money is going to be the main kind of driver in the discussion because as a company, we try to be as transparent as possible and whenever we hire anybody, I say to them we publish our salaries, we share them internally, we’re a bootstrap company so there is no long channel of cash that’s available so you have to be OK with that. And basically I will pay you as much as I can and as generously as I can but there isn’t really a sort of negotiation. And anybody that’s weird about money, I think it’s not gonna be right for our company.


So we follow up on our references, it’s really important. If someone is gonna be weird about what they say, they don’t give you their references or…I would very happily take up a reference from the previous employer before I’ve made an offer and then from the current employer once I made an offer. And you talk to them about strengths and challenges and try to give them as much opportunity to give you a sense of who the person is that you’ve hired.

Video Calls

So then the stage of turning out all those no hires we then have a video call and at that point it speeds up and I recommend that you don’t want half of your company sitting around a laptop for an hour on somebody you know was a no hire in the first 5 minutes. So we only schedule 20 minute video calls and we’ll try to keep is down to as many potential hires. Any no hires that we can exclude at this point we will because we’re starting to seriously waste company time on potentially no hires. So we might interview 4-5 people for 20 minutes and really at that point, it’s a sort of stop go moment. We have had video interview panels where we just haven’t found anybody, there’s been nobody and we managed to exclude everybody before at every stage we’re looking for a reason not to hire. It’s really positive if you want to work for and you watch me. We don’t wanna hire you! So we’re looking for reasons not to hire you because one of Joe’s advice is that it’s a terrible mistake to accidentally hire a no hire or maybe it’s not ideal to overlook someone who might be a good hire but you didn’t hire them, it’s really a state that you have to reverse later, through firing them, if you make a mistake. So but of course at some point you have to say if not them, then who? You get to a point where you can’t find a reason you think well maybe if it’s one of these guys, then I will hire them. Somewhere you have to take the leap and say this isn’t gonna be my company, we’re branching out and hiring new so there is this final stage which we do which again I copied that from buffer which is we have a 3-month contract which is a sort of a suck it and see moment for both of us because by that moment you found somebody who is as interested to know if they will fit working for you as you are about whether you want to hire them and that’s the kind of person you should be looking for. Interested in what you can do for them as well as the other way around. So that 3 month contract will be set up in different ways depending on the country in which we’re employing but it’s an opportunity to get a face to face and direct work in relationships. So set up and we know what it feels like and we will fly people around the place, we’ll have colleagues in the US meeting them or fly around people in Europe so that we actually have people before after a 3 month period, this is hopefully what we’re going for, which is that we have done it and we’ve made hire! And I’m all 33 Mark so we’ve got time for questions [cheering]!

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Audience Question: I also have a small software company and I was curious on your things on hiring. You said you like to hire bright people and the examples you gave suggested you like to hire experienced which to some extent when you’re trying to do something new can be a double edged sword. Where you are on the spectrum of it insisting that people are able to do the job you want from day one versus people who can invent a job for themselves or not have the experience but hit the ground running?

Bridget Harris: That’s a really good question and we’ve done both actually. So the only downside to being a remote company, and we’ve had experiences of this, is that it’s very hard to hire junior people remotely because they do deserve more support and training, no matter how bright they are. You’re the ones hopefully are trying to channel them. So we did have a junior tech woman who worked for us and she went to be a software developer for computer games so we couldn’t stop her cause she was a games designer. She worked for us in the office and was brilliant and would have loved for her to work for us and build her up, even though she didn’t have any experience with what we wanted her to do. So I can see that if you’re – that’s the mind-set of the company then you can essentially set yourself up in order to do that, but for us we don’t have that luxury so we’re looking for experienced people but all of the people I’ve hired are essentially senior managers so one of their jobs is to be able to do everything about their job now and then to hire people down the line as we grow to sort of break it up a little bit. So you’re not looking for only experienced and smart, but also a range of skills and people who don’t mind getting their hands dirty and being able to do a whole load of other things, cause being in a small start-up with 12 people everyone must muck in. There were some people we hired who weren’t at the point of the senior manager we were looking for and we came to a conclusion. We extended it to 6 months and let’s see what you can achieve in these 6 months. And in a way, going back to the ship that we want to be on, part of it is about empowering people and giving them internal motivation and autonomy to grow their own role within the company. So I would always hire smart and experienced over smart and inexperienced because as I said from my experience, the resources you have to put into that, unless you’re a big company, is not something we have a lot of to do.

Audience Question: Aside from hiring what are the other key challenges you encountered in remote working? And how did you overcome them? Because it’s a new concept.

Bridget Harris: So in a way it’s to avoid being dragged into the Bedford thing as I said me and Keith live in Bedford and there’s another full time senior person and it’s the communication, adoption of what you’re going to do. It doesn’t happen by accident and it’s not an easy thing to do. So everything about our project management and the way we share and collaborate and we use video tools we have chat channels and all the channels we’re using to share during the day as a team, we do it consciously and actually say to people when they are not like that, if you’re going to work remotely you have to be part of more of a social virtual thing and I think that will become more of a challenge as we get bigger cause now we’re 12 and it’s very easy to spot everyone and what they’re doing. But as we get bigger, I think we will have to more and more enforce the fact that people can’t have offline conversations and I’ve banned email for example. Everyone that starts get an email from me saying don’t email me because when you think about it, email is a communication spur, it will end up in people’s inboxes and then you have this weird reply thing, slightly aggressive BCC thing and everyone is trying to channel through email and it’s just horrible.

Bridget Harris: Donald Trump said that!

Mark Littlewood: He doesn’t do the email thing! Maybe that’s the one thing I agree with Donald on. I say you can’t do email because email removes the opportunity for other people to see what you’re saying in the company so everything as discussed and we have that transparency ethos.

Audience Question: Before you jumped into hiring people full time, did you go into any fears of having freelancers and contractors? If so at what point – what do you feel is the right point to move from that to full time staff and what are the pros and cons?

Bridget Harris: So it’s about the demands of your business so looking back we should have hired full time support people much earlier so there was too long when Keith and I was doing support when we should have hired people to do that job and I think it’s the impostor syndrome that I was talking about before that it takes you a leap. And this is where maybe VC’s or investors have a good role to play cause they do expect you to scrub you earlier and it took us longer to hire. We should have hired much earlier in a much more confident way but that 3 month contract that I was talking about, in the US we will employ people for 3 months and they know it finishes in 3 months and during that period we then discuss whether we’re going to extend it but in Europe it’s happened where people were on freelance contracts and it takes time to set up. We wouldn’t take time to employ someone in a country we know we won’t hire them. So most remote people in Europe have started on a freelance contract and then if we’re all good to go, then we can set up to employ them directly. But I think that the second freelance contract can only work for so long because we do have somebody actually on our books who works for us on a regular basis who is a freelancer. I personally believe that if we’re building a company and trying to grow, I want to hire people because I want people to be part of the growth and part of the company’s history and what it wants and I have been a freelancer myself for years and years. And I think the problem with freelancers is that they are hedging their best and never committing so we are actively looking for people who want to be part of our ship and not sort of dip in and out. Although it’s a very useful tool when you’re trying to manage your finances and cash flow and trying to get things done. We did this once and we didn’t do it again, we used one of the agencies who promised the software developer out of a box. It’s out of a box! It’s a month and low risk and we will give you your money back and I feel like this chain gang of software developers in some remote places that are ready to work on your project and they email us all the time and recruitment agencies and I say no to all of that because I am trying to control the process because of my success at whittling down and finding the people who worked as hard to find us so often the people we hired were the ones who worked as hard to find a company like us to work for as the other way around.

Audience Question: Thank you! It’s great! I was curious about the process that you described for sort of blind hiring. Where you have multiple answers to questions. Can you describe that format and do you use any specific tool to get that in front of your people? Maybe you can just explain that process.

Bridget Harris: Absolutely! So when we hire a couple of developers, we advertise in stack exchange and I control all the process and I was the one managing all the applications and communicating with them and stuff and we ended up with a short list and I sent it that Keith and Antonio were the ones who actually did the short listing so I removed all of the personal information about those answers so they could just see 10 answers. And they short listed 5 from that and I’ve got to say one of those people was a woman and I was really pleased in terms of the challenge of hiring female engineers that I knew she had got in on a short list on the basis of her answers alone, and nothing to do with her experience or background, told me it was a positive process and I think what you said about diversity as well all the other unconscious bias that you get in selection where you think – cause you look at 20 people and you have your favourites and don’t realise that that bias is coming in to find people who are familiar to you. In terms of female engineers, we also have a reverse problem we don’t have any male customer support people and we’ve really struggled because we do exactly the same process and Kate will do all of the short listing and then if there’s a- we used to interview together and realised we had similar reactions to most people. I would come in and interview 2-3 people and I would know nothing about them. So you’re now at the final stage interview and I know nothing about you so this is your opportunity to tell me and give me a sense of why you could be working here. It’s that opportunity of fresh eyes. When I did it – I got slightly obsessed with it and the head of operations and it was when you fill out the application, don’t tell me your name or anything else about you! Just put in your mobile phone number and I will track the application from the stuff that I had using our ATS so in case anybody has a dozen users, I recommend using some software that manages applications and puts it into of systems because when you deal with 100’s of applications you can’t deal with the PDF and it’s crazy! You need an application and funnel that is managing people through and yes, the mobile phone number thing worked really well because it meant that I could have 20 people who had all put their mobile phones in so that I could read the questionnaires and it annoyed me when people would put stuff in their answers which revealed to me where they were. I was like if you’re gonna be my head of ops I would want you to understand why I want you to anonymise the data and now you’re making it clear who you are so you’re trying to sabotage my attempt so that becomes a no hire. You have to be able to understand this process because ops will then themselves do this process and will be the ones that have to push it forward next time. Or someone put a different phone number to the one in their application so no, I can’t track you now, I don’t know who you are cause you have a different phone number. Then what happened was I didn’t do the Skype interviews for those 5 people cause I was obsessed with them and that job was about replacing a lot of what I’ve been doing for the last couple years so Keith and Kate I gave them the 5 people I wanted them to interview and 6 questions and I said just ask them these questions. Don’t busk, don’t improvise! Just do these 6 questions. So they did them and didn’t have any idea of who these people were so they came to it fresh and they haven’t got their biased built up so they came to me and said right, this person and this person. The other 3 weren’t suitable but we know you could work with these 2 and then those 2 came to Bedford and I did a long one on one interview with them so it has to work in different ways but you have – you’re kidding yourself if you don’t think you have yourselves biased or favourites. Stack exchange came back to me and asked me how did it go? Because they were trying to evaluate their program. I said to them, recruitment job boards people should think a lot more about taking personal details away from the way they advertise because stack exchange could further the interests of a much more diverse range of engineers if they stopped with the opportunity for that rock star marketing and advertisement that so skews people’s views.

Mark Littlewood: Everyone is a rock star ninja if you’re a coder! Any more questions?

Audience Question: How do you handle the nightmare that is US payroll?

Bridget Harris: So I’m sure that all of our clutch and accountants and lawyers would have a LinkedIn account by now because they have to set up logistically. In the US our lawyers advised us get an employer’s agency so you will get a company in America to do it all for you and it’s undoubtedly given my experience since then, I realised it’s a nightmare cause you want to employ someone in Georgia, you have to set up the company in Georgia so we’ve got an inc. company in the US and we have to do that first, then we have to set up in a particular state that we want to employ somebody and they need to know about payroll and everything else and that costs money to do that. Even though it’s more expensive and a pain, I want people to have on the payslip so I didn’t go down the route of the arm’s length employers’ organisation that can do it all for you, partly because I think we will hire more people in the US. Having said that though, it’s a complete pain so we have an accountant in the US who manages all of our sort of money back and forth it has to go there to pay those guys, we use what was called Zen Payroll but now it’s Gusto which is a pretty good application, it will handle all of your state, filings and tax withdrawals from pay packets and so on so that all happened actually with the power of the cloud fairly straight forwardly and easily and the things we have been tripped up on is more of the state legislation to do with compliance. When you got to get workers compensations and insurance in another state but you don’t need it in another bear and the biggest problem is that it’s almost impossible to get health insurance for multiple employees if they live in the US. So not only do they need only one person you can’t just get group healthcare for one person. The healthcare insurance providers like them all to be in the same state, they don’t like people out of states to where you are registered. So if we’re not registered in any state, then we won’t get it but we’ll do a different scheme in NC to the one in Michigan and it’s a complete nightmare. And we ended up with – and I don’t understand it because I’m not trying to not pay it. I really would like to pay good healthcare, I’m paying good top dollar and where do I do that? They’re like no, you can’t do it. So we ended up with personal healthcare for our employees because it’s almost impossible for us to do that. So that’s another remote problem, that remote is difficult in the US unless you get to a point where you can start – you have enough people in one state to justify a group plan. So hiring in the US is very hilarious because it can really take as long as 2-3 months as it did in Spain and I have a – we have our Spanish account and it’s good and we found them through European network, enterprise people who would give us advice, in Spain everything needs to be translated twice, contracts need to be translated twice, everything has to be stamped on every page and get the apostle thing stamped, corrected in Spanish, sent over by courier. The whole thing takes months and our accountant will every month when we do the payroll she says please send us the receipt we’re their representative in Spain. And it’s a formal and scary process and very thick with paperwork. Ireland, we can just set you up, don’t worry! You just pay her, we will set her up as an employee by the end of the month. Really? You don’t want anything translated or stamped? No. So in Ireland it got in literally half a day and the accountants were absolutely brilliant and then we run payroll and we use software which we’re coming to the end of our ability really in terms of it’s generally for small businesses and we’re kind of outgrowing it a bit but they’re doing well because all the payroll for Ireland and Germany is another place where we will set up and I heard it will take a couple days and so all that payroll comes through into 0 and then it just gets processed as a normal UK cost but we’re paying tax, social security and employment benefits and stuff and they have their own European countries contracts all in those countries. So we would be a big loser if the UK left the EU [laughter] just as a little thing!

Audience Question: Thank you very much for the talk! I just have a small question. How do you go about funding your new hires? You mentioned stack exchange, but how do you go about it? Do you use other things as well or only that?

Bridget Harris: So people coming – we advertise on Stack Exchange, I wasn’t really happy if I’m being honest with the diversity of the applications, I would have preferred to have a much wider pool. On the other hand, we made some good hires on that process. It all depends on the job, we’ve had people who have speculatively applied to us who end up working with us. We found them by word of mouth so when we’re looking for a developer, we went through an entire process on there and nearly hiring – and the person we ended up hiring came through the network in Spain. The problem is people’s networks tend to be similar to their networks and as much as we’re hungry to hire talented engineers, business wider arrange as I possibly can, if anybody hears this and has an opportunity for public forum, it’s that I would like jobs boards for all of the diversity that is going on in terms of coding and engineering and encouraging more people that haven’t come from a traditional background, whether that’s not just women and girls but anybody from any non-white background I would really like to know where those boards are and as companies who are really committed to that inclusion and openness where we can go and advertise. And we’ll always spend a couple quid on a job board if I feel like it’s trying to reach many people, to get our advert out there. I hope that helps it’s something – we are advertising particularly targeted at remote workers so that comes out from a completely different perspective if you are in Seattle and people need to move or live there to work for you. We’re very agnostic about where anybody is!

Mark Littlewood: Fabulous! I think that’s all we have time for!

Bridget Harris: You can meet Keith! He’s the CTO! I’m very pleased actually that Rand was also talking about being a husband and wife team cause we are – if anyone is thinking they’re very close, those two in the conference. We’re actually married and that’s also made it and answered a lot of questions that people have raised about co-founders because for me and Keith we are co-founders, but sharing 100% of what we’re doing. So we’ve got an opportunity and a good blend of tech skills and management skills that you would need for any company so I don’t know if you want to say anything. No, you see?

Mark Littlewood: Tech skills to the fore.

Keith Harris: I’ll just say hello and be gone!

Mark Littlewood: Brilliant! Keith, thank you so much!

Bridget Harris: Thank you!

Bridget Harris
Bridget Harris

Bridget Harris

Bridget is co-founder and CEO of YouCanBookMe

Bridget’s is the founder and CEO of YouCanBookMe, her third career.

Her first was in the television and film industry before switching to politics.

She served primarily as a policy adviser, with wide ranging interests including the role of technology in society, equal rights and opportunities. She ended up being an advisor to the UK Deputy Prime Minister.

In 2012 she started working full time at YCBM where she deals with YCBM people, business, legal, finance and strategy.

The service now manages over 750,000 appointments a year for companies including TED, Uber and Netflix as well as a huge number of SMEs.

More from Bridget.

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