Advice for Startup Advisors

CB Insights ran an amusing Tweetstorm that poked fun at their favorite startup advice cliches. The discipline of advice-giving is a contentious one in the startup ecosystem. Providing effective advice is quite a skill and there’s always scope for improvement. For mentors, coaches and board members who deliver advice, and as Founders and CEOs on the receiving end, I’ve collated some of the best resources that I’ve come across to help us go a little deeper in thinking about this challenge.

If there are any helpful posts, books or other resources that you think I’ve missed then please add them in the comments.

Finding your purpose and living a meaningful life

hunter-s-thompson-early-self-portrait-on-the-road-to-tijuana-1960sHunter S. Thompson’s letter to his friend Hume Logan is worth a read for many reasons, but Hunter sums up one of the biggest challenges of giving advice in the opening paragraph of his letter:

“You ask advice: ah, what a very human and very dangerous thing to do! For to give advice to a man who asks what to do with his life implies something very close to egomania. To presume to point a man to the right and ultimate goal— to point with a trembling finger in the RIGHT direction is something only a fool would take upon himself.

I am not a fool, but I respect your sincerity in asking my advice. I ask you though, in listening to what I say, to remember that all advice can only be a product of the man who gives it. What is truth to one may be disaster to another. I do not see life through your eyes, nor you through mine. If I were to attempt to give you specific advice, it would be too much like the blind leading the blind”.

7 Tactics to Get the Most Out of Your Startup’s Advisors

Phin Barnes at FirstRound has written some excellent articles on this topic. My favourite quote from the article talks to a coach-approach (which I have an inherent bias towards):

“The entrepreneur often already has the best answer. A good advisor will bring it out by forcing them to walk through the problem again and again”.

Dear startup advisors, you don’t always need to be right, but you have to be solid

Phin Barnes does it again with his leaning towards a coach-approach i.e. don’t just tell people what to do, but facilitate a conversation that lets them come to their own conclusions. Here’s two choice quotes.

“I could never get a solid grip on advice summarized by, “I’ve seen this before + instinct = decision.”

“In my experience, you shouldn’t look for advisors who give you an answer on a silver plate… Instead, you have to push for well reasoned, well researched, strong opinions that stand up to your analysis. You have to demand that your advisors offer solid advice that you can latch on to and use to pull yourself up or push against to spring forward in the opposite direction. You need guidance from people who aren’t afraid to unpack their instincts so you can choose the best, recombine it, and leave the rest.”

Startup advice should be strong on the ‘why’ and the ‘what’

Nic Brisbourne at Forward Partners builds on Phin’s post and concludes with his own advice to Founders and CEOs:

“Help advisors unpack their instincts and explain the ‘why’ as well as the ‘what’. When advisors are drawing on experience ask questions to explore what they are remembering, why things worked out well last time, and then get into detail on the similarities and differences between the what happened in the past and the current situation. Most advisors will welcome this discussion, it makes them smarter and makes them feel valued. Conversations where advice is passed and then ignored are much less satisfactory.”

Tips for productive advisor-entrepreneur conversations – argue intelligently and criticise kindly

Nic builds even further by explaining the problem in being too direct when giving advice and hence the importance of focusing on the ‘why’:

“A common pattern is for advisors to pattern match with something they’ve seen before and come quickly to a piece of advice that feels right to them. That’s great and hugely valuable when it chimes with the entrepreneurs intuition, but when it doesn’t the dialogue can deteriorate to brute force persuasion and sullen acceptance or passive resistance.”

Be helpful, not right

One more from Nic in which he summarises the difference between a mentoring and coach-approach (a topic about which I shall right more):

“When mentoring, the first instinct of many of is to jump into solution mode and try to fix problems by suggesting solutions. Often the advice is framed as “I’ve seen this situation before and you should do X”. That’s a direct coaching style and is appropriate in some circumstances, particularly in the very early stages of a company where there’s lots of things to do and the founder doesn’t have much time to think about any of them. A non-directive coaching style helps the founder to think through the problem and come up with their own solution. It takes more time, but is often more powerful, particularly if the situation is complicated and the match with the mentors previous experience not perfect.

Simply giving the right solution to a founder is no use if they don’t understand it or internalise it well enough to implement it properly, or it hasn’t been explained well enough for them to tweak it to their precise situation. In these scenarios it’s better to help founders think through the problem a little bit, even if they don’t get to a final solution. Best of all is for them to have the right solution and be fully ready and able to implement it, but that isn’t always possible.”

Startup mentoring, the Socratic way

An excellent post from Fred Destin at Accel Partners, highlighting the Socratic Questioning approach towards helping startups. I really like the way he tees up the relationship:

“Step one in mentoring is establishing a protected, trusting environment in which your protege will feel free to quickly dig into the important issues, expose doubts and shortcomings and be disposed to make real progress. Your job as mentor is to make the person feel relaxed and intent on thinking through their own business issues.

If you want to be helpful to someone, you’re not going to achieve that just by rehashing experiences that worked for you. Step two is gaining an accelerated understanding of the unique person you are dealing with and the unique problems they are facing. Ask the person in front of you what it is they do and what they are dealing with.”

Be a Trusted Advisor

That Fred emphasises the need to build trust before doing anything else is brilliant. I also like Fred’s reminder to “calm the impulse you have to be immediately adding value”. Here is a quote from The Trusted Advisor, one of my favourite books on the subject of giving advice.


The quote highlights two important factors. Firstly, that trusted advisors make a pronounced shift from being just technical experts (and delivering direct advice based on pure expertise) to being someone that can “help clients see things anew or to make a decision”. Secondly, and back to Fred’s point, we’re reminded not to dive straight into solution mode. As a coach, I can attest to the fact that many clients take enormous therapeutic (and in turn practical) value from first just being listened to. First understand the problem, and THEN you can help someone to solve it.

How You Know

Paul Graham from Y-Combinator hammers that point home in his essay How You Know. He quotes the great mathematician Hilbert who:

“had no patience with mathematical lectures which filled the students with facts but did not teach them how to frame a problem and solve it. He often used to tell them that “a perfect formulation of a problem is already half its solution””.

Here is How to Make Sense of Conflicting Startup Advice

For Founders and CEOs potentially drowning in a sea of advice, this post from Mark Suster is great. His key message is to triangulate all the information, a mathematical term he explains is:

“Used in sailing and other activities to help you better navigate when you don’t have your bearings. By having the measurement of some known points you can better navigate to unknown points through inference.”

He concludes that:

“Saying not to take others advice is itself terrible advice. Take more advice. Mix people’s views into a cup. Stir them around. Think about the motives or experiences of those offering advice. Think about whom you trust based on past advice. Think about your own situation and overlay it against the frameworks that others offer. Triangulate. But in the end follow your own gut. That’s why you’re a founder.”

A Template of Terms for a Potential Startup Advisor

Finally, if you are an advisor (in whatever capacity) or a Founder / CEO establishing a more formal advisor-company relationship then this Template looks very useful.

Please note that I have not used it myself and I also expressly disclaim any and all responsibility and/or liability for any loss or damage whatsoever arising out of or in connection with acts or matters done or omitted to be done in reliance upon this document  😉


My name is Richard Hughes-Jones. I am a Coach, Consultant & Lecturer who works with entrepreneurs. My clients are CEOs and leadership teams of startup and scale up businesses. I am an Associate Lecturer at the London College of Fashion and retained Consultant to the Centre for Fashion Enterprise.

I previously gained over a decade's experience as a Deloitte management consultant and HM Treasury civil servant. My full profile is on LinkedIn and you can also find me on Twitter. If you'd like to receive my book reviews you can sign up below.