About a year or two after starting Red Gate (this must be about 10 years ago now), Simon and I were chatting to a couple of venture capitalists. We explained what we were doing – building software that we hoped people would buy; software that addressed the pains of SQL Server developers; software that people would just download, try and buy.
A few minutes into this conversation, one of the venture capitalists turned to us and said (and I remember this vividly):
VC (confidently and suavely): "You know what you need?"
Me (eager to learn): "No"
VC (authoritatively): "A strategy. That's what you need. A strategy."
That conversation has stuck with me for over a decade. It epitomises the problem of giving advice and illustrates why I find giving advice so hard.
Everybody's situation is complex, full of subtleties and unique. The idea that I – or any 'expert' – can give you advice after a ten minute chat over coffee is laughable. The advice will either be generic ('you need a strategy', 'just ship the product', 'talk to your customers'), wrong ('what you need to do is hire a PR company' / 'under no circumstances hire a PR company'), or both (in our case – a case with its own special set of circumstances – not having a strategy and simply trying to build software that people wanted worked out fine).
The best advice I get is when people don't tell me what to do. It's when people use their deep experience to ask interesting questions that make me think, or when they describe similar situations they've been in – with all the details and context – and explain the choices that they faced and the decisions they made with all their pros and con, and why they think they worked, or didn't.