Entrepreneurial Advice: Tough Love better than Cheerleading
May 9th, 2016

Entrepreneurial Advice: Tough Love better than Cheerleading

In my role as an adviser to founders of startups, and after 30 years as an entrepreneur, these are some reflections on the topic of giving advice, and how to best receive it!

Your comments and suggestions are always welcome!  

Are you looking for advice or validation?

Have you ever asked for advice even though you have already made your mind up? All you really want is someone to validate your thoughts and decisions. Sometimes you simply need a sounding board to force yourself to express your thoughts and opinions, and you might not even listen to the response as you are already working on how to execute your plan.

The problem starts when your sought out adviser starts to disagree with your preferred solution to a problem, or throws you some challenging questions on why you should look at the problem from a different perspective.

As an entrepreneur you might feel that it’s your job to be opinionated, take firm decisions, be confident and not waste time getting everyone’s opinion before acting. So why even bother with advisers, coaches and mentors if you think that all they do is sit on the side line offering general advice, without having to deal with the reality of getting s**t done every day?

Advisory – It’s a trust thing

There are, of course, no real truths about how to be an expert adviser or how to be the best “advisee”, but there is no question that surrounding yourself with experienced advisers who have been down your path before (starting, building and exiting tech companies) are worth listening to. Especially if they genuinely listen and engage at a detailed level to truly understand your context and specific need for advise at any given moment. Good advisers know how to do this and build a trusted relationship where it’s OK to completely disagree with you.

“Tough Love” is caring

In fact, in many cases you may have given up a safe salary, betted your whole life and savings on your own startup company, and you are naturally looking for people to cheer you on, give you a pat on the back and accept invites to all sorts of entrepreneurial conferences. It might be counterintuitive to go looking for advisers that will constantly poke holes in your plans, point out how flawed your business model is and tell you to not give up on your day-job until you have enough revenue flow to pay your rent and basic outgoings. But these are the advisers you should be looking for, because they care for you a lot more than the well-wishers who will not guide you through what is a road fraught with potholes and wrong turnings.

In my job as an adviser to entrepreneurs of all ages, genders and experience, I find it fascinating to see how advice is asked for, received and used. I take my advisory role seriously and care a lot for my clients, to the extent that I will confront them head on if I think they are making the wrong choices. They also know that I do this to help and not to win arguments about who’s the smartest person in the room. We often hug as we meet and as we say goodbye. To call it love might be exaggerating but it’s certainly a relationship where both the heart and the brain are involved. So let’s call it tough love!

I too used to be a young CEO, a founder of startups and remember who I really trusted, and who I felt was just talking at me, or always agreed to whatever I suggested without challenging me (which is probably the worst kind of adviser).

Make it personal and improve

The adviser that I found the most valuable was the one that understood who I was as an individual and helped me solve the problem my own way whilst learning in the process. This often took the course of helping me to outline the real options to any specific problem through conversations, usually outside the office in the early mornings or evenings when you have time away from the daily grind. What I appreciated was also introducing me to other advisers when they admitted that they could not add value or know-how in a particular domain.

I believe that this brutally honest coaching style is the way forward to build incremental knowledge for both the advisee and the advisor.

Everyone’s clearly different and have a mix of experiences and there is no one-size fits all art of developing adviser relationship. But I believe that both sides of the advisory table can continuously improve their skill and find the experience rewarding, as long as it´s based on 100% caring for the success of the entrepreneur and the business.

This article by Harvard Business Review is an excellent guide and provides practical suggestions to improving your skills for both giving and receiving advice, based on research and actual case studies. I recommend reading it and asking yourself where your areas of improvement lie.

Choose advisers carefully – 6 key points

To summarize, these are my top 6 things to remember when selecting your advisers:

  • They care for you deeply as a person who wants to succeed
  • They are brutally honest and welcome conflict as a way to make better decisions
  • They have been in your situation and know what it’s like to run a startup
  • They are available 24/7 to take your call and help out
  • They are willing to work on compensation that is biased towards success
  • They are willing to seek advice themselves and acknowledge that we are all “students for life”

That’s my best advice of the day 🙂

Tough love to y’all!


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