How to Evaluate Yourself as a Business Leader


In my last article, I posed four difficult questions that every business owner or CEO needs to ask themselves.

They are:

  1. Who appraises you?
  2. Who challenges you?
  3. Who guides you?
  4. Who replaces you?

As you will have noticed, the first three have significant overlaps. The fourth sits apart. So, I will attack the first set here, and cover ‘replacement’ or, your ‘evolution’ within the business in a separate piece to be published on the website soon.

The first step to appraising and challenging yourself, is to admit that you can’t do it alone. Self-awareness is all very well and good, but it is crucial to have someone else to help guide you and offer fresh perspectives. And as much as I attest to the power of open communication within a team, there are times when it’s best that you confront your issues and fears away from colleagues.

There are all sorts of people you can turn to for support. The suggestions below appear chronologically in-line with the maturity of your business:

Someone Close

At first, the best advice is likely to come from a family member or a trusted friend.  If you’ve recently started-up, you’ll be all hands to the pump. It’s as likely that you’ll need emotional support and a bucket of common sense as your new business takes root. Speak to someone who knows you well enough to tell you the truth. If you look awful, if you seem to be rushing down blind alleys or if there’s something you’ve clearly missed, they need to tell you right away.

The challenge is to do so within a consistent context. Try to avoid asking different family members questions that reflect their specific skills or experience. They won’t get the full picture. It’s more advisable to ask someone close to chat more regularly so you can build on their wider understanding of you and the business. 

Network & Learn From Those That Have Been There Before

As the business begins to grow, you’ll start to spread your wings. At this stage you might not be ready to employ a coach or adviser, but you’ll be meeting a range of people at networking events and friendship groups who will be happy to pass on their advice.

They will happily lend an ear, whether it’s to validate your thinking or suggest something you might have missed. It may be early in your story, but anyone running a business will also be keen to hear about your experiences – this can be a reciprocal relationship where you benefit from each other’s challenges and successes.

Formal Advisor

There may be one or two people you meet in this way whose words resonate. You might find that you start to adapt your business as a result of their insight. It is worth asking if they would like to take-on a more formal advisory role at this point. That doesn’t necessarily mean paying them. It could just be a monthly breakfast (on you!) where you feel free to ask questions and receive their advice. In my experience, it is amazing just how much entrepreneurs want to give back. Many won’t see this request as an imposition at all.

A Business CoachSelf Evaluation, Board of Directors, Business Coach, Business Advisor

This is a professional who you pay to get to know you and your business. You book-in a regular session with them and they give you dedicated insight and support. An experienced coach will have numerous case studies to draw upon, many of which will be directly relevant to you. Like your trusted friends, the coach is also someone to whom you can say anything in confidence. It can be well worth the investment.

An Unofficial Board of Directors

Your ‘unofficial’ board doesn’t need to be paid. It could just be a handful of friends or contacts who have been particularly helpful to you along the way. They will be flattered to be asked, and if your ‘ask’ is that they join you for a group coffee or meal every quarter, you may be surprised at how keen they are. Selecting a group with complementary skills is crucial. You could offer them a small equity incentive for their support. This would be no bad thing as it gives them a vested interest in helping you thrive.

Board of Advisors

As the business grows and you meet new challenges, don’t feel that you should only develop this relatively formal advisory relationship with one person. I find it helpful to listen to people outside the business with different experiences and strengths. One person may be able to offer you brilliant advice on your marketing strategy while another is up to date on employment law. You’ll quickly find areas where your advice and burgeoning experience is equally relevant and pertinent to them.


Businesses can become all-consuming. They can have a huge impact on a founder’s self-esteem and mental health. A therapist can listen and support you on how you are coping. They will listen and respond to your motivations and fears. Please don’t see this as a weakness; in fact I’d suggest that spending dedicated time on yourself in this way can be just as beneficial as business-related support (except ours of course!).

An Official Board of Directors

You have reached a point where investment in your business means you have third party shareholders to please. Your investor will want a board in place to advocate for them and I suggest that you see this as an opportunity you can grasp proactively rather than waiting for the investors to take charge.

At your monthly or quarterly board meetings you will update them, ask for support and call on their experience in specific areas. They will begin to sign off important decisions in an official capacity. Your words will be minuted and your goals shared. Suddenly, your business has grown to a point where you are no longer the ultimate arbiter. That can be quite a shock, but it’s a sign of success.

These different sources of help and support reflect your development. What’s crucial is that you don’t wait too long. It’s amazing the benefit you can glean from an open, honest conversation about you. From the very start, it’s best to share your hopes, dreams and challenges than to bottle them up. One day, there may be a boardroom table around which the great and good discuss things with you. In the meantime, I’d ensure that you surround yourself with people who want to appraise, challenge and guide you.

Lorne Asks:

  1. Who was the last person you turned to for advice?
  2. Could you take some time out to run through this list and see if any of these people could provide the support you need? Would they help answer the four questions at the top of the article?!
  3. Why not scribble down your ‘dream’ unofficial board and then ask them out for dinner?

About Lorne Noble

Lorne loves finance so you don’t have to (seriously, he plays with Excel sheets on vacation)! He spent 12 years in corporate London as an investment analyst then made the jump to Boulder, Colorado to act as finance mentor to high impact companies at The Unreasonable Institute, Girl Effect Accelerator and Singularity University. He has an MBA from IE business school in Madrid, Spain.

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