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Ask This Question to Your Advisors

Written by Dave Bailey

Woman asking her advisor a question

The key to a successful relationship with your advisors is asking them the right questions. Learn the best question you can ask an advisor here.

I’m part of a large startup group on Facebook called ‘London Startups’. Every so often, a founder posts some designs and asks for people’s opinions on which to build. Inevitably, votes are split between the options. Finally, someone chimes in with, ‘Just run a quick A/B test.’

I completely resonate with the near-constant need founders have for advice. There are so many decisions that need to be made that it can be overwhelming. To make things worse, there simply isn’t the traffic or resources to run split tests for everything. And that can leave you feeling completely alone.

Good advice is out there and it can help you learn faster. In some cases, it’s quicker to get good advice than to run a test. But the secret to finding good advice lies in how you look for it.

The old model of advice

I used to think about advice like this: you give someone a summary of the situation and then ask for their recommendation on what to do and why. But I kept running into a familiar problem.

If I asked 10 smart people for advice, I’d often end up with 10 completely different and opposing recommendations. I felt just like that founder in the Facebook group with split votes for A and B, and a recommendation to collect data that just wasn’t there. It was frustrating — especially when I was really hoping for a consensus to make my decision easier.

A better model for advice

As I’ve matured as an entrepreneur, I’ve realised that no-one else is better equipped to take decisions about my business than me. And to make better decisions, I need to better inform myself.

So rather than asking what people would do in my shoes, I lead with a different question:

‘Have you been through something similar before?’

Ultimately, I want to dig deep into the specifics of other people’s experiences to learn from their successes and their failures. Knowing the details is important because that’s where the real insights lie. It’s helped me understand why smart people can arrive at very different conclusions.

The question also separates the intelligent guesses from the voices of experience. Intelligent guesses can be helpful, especially when they spark creative new ideas. But dissecting a real-world experience where the outcomes are known — and being to able to ask things like, ‘How happy are you with that outcome?’ and, ‘If you did it again, what would you do differently?’ — is extremely valuable. 

Those who ignore history are doomed to repeat it

Having been around startups for a long time, I’ve seen that they all tend to make the same mistakes. Company-building is counter-intuitive, and naive approaches don’t work like you imagine they would.

As an investor, I see companies follow the same learning processes in many areas, from sign-up forms to online marketing, from recruiting to sales. When you’re stuck in the weeds, your problems can seem unique to your market, product, or company. But, if you know where to look, you’ll find others that have faced — and overcome — similar and bigger challenges.

Tap into someone else’s experience

Once you understand that advice is really about leveraging other people’s past experiences, you’ll find that it’s more readily available than you thought. For example, that Facebook group I mentioned has 30,000 entrepreneurs who have collectively run tens of thousands of experiments for you.

I don’t want to discourage you from collecting data. But before you spend resources running a test, first consider finding someone who’s already run a similar experiment, and see what can you learn.

Continue reading about business advisors:

Originally published Mar 11, 2019, last updated Aug 19, 2021

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About Dave Bailey

Hi, I’m Dave Bailey and I coach tech CEOs from Series A to pre-IPO. Join 20,000 entrepreneurs who receive my new essay every week. 

I will never sell your information, for any reason.

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