strategic consultant to:  

~ serial CEOs & CTOs in software, Internet, technology & digital media
~ experienced consultants in all fields to maximize their practices

Even with your founding team, you are often isolated in your role of CEO. Yes, it is the time you’ve always longed for, and you are excited and grateful for the opportunity to take your best shot at a new venture (your first or your next). And you are moved by the loyalty of your team, and the risks they are willing to take to share in this vision.

But still, in the middle of the night, or the middle of a meeting, there is that feeling that you are so alone, and that need to share your questions, and even your worries, with someone who is watching out for you first, with an eye to the success of the Company you are building. You want someone who is not dependent upon you, who will tell you the truth when you don’t want to hear it, who is not afraid of being fired, and who (from deep experience) can see the larger picture of the success of your Company in your industry. Someone devoted to your success as a CEO.

Who is this person? It is not your employee, who is dependent upon you for his or her success (and paycheck). It is not one of your early founding team, who is working for minimal salary but does not control the destiny of the company by his or her vesting shares. It is not your life-partner who may be dependent on or protected by your income, and who is sharing the risk with you.

Of course you can share a lot with your life partner and your co-founders, and life is easier when you can. But they have, rightfully so, their own agenda and visions. And not one of them sits in your chair, needing to make your decisions, and taking your risks.

If you are like most entrepreneurs, your role as CEO has involved your taking the greater risk than the others: more personal capital at the outset, more lost opportunity and time spent on the “hidden year” getting started and not getting paid, and the responsibility for changing or refining the direction of the Company from your earlier visions.

And the farther along the Company grows in its success, strangely, the more remote you can become in your connection with the team.

More success can often mean more risk, and different risks, and longer times of risk. Just when you would think that new successes would solve the stress you are carrying, all that happens is that the stress changes — for you, and for the team, often in different directions. The team becomes more focused on implementing their departmental roles, and your role as CEO becomes more outward-looking – to your Board, to your investors, and to the marketplace and capital markets that need a spokesperson and visionary.

You find you cannot share everything you know with your team as you did in the early days. Everyone seems to want something different from you – more time, more attention, and more budget — more of your bandwidth that is always under pressure.

So, who is looking out for you? Who is showing you how to allocate your bandwidth, who is listening to what you need — with no agenda but to make you the best CEO you can be, and this venture your next success? Who is helping you keep your perspective, and your focus on the primary goals, and validating or questioning your priorities? Who is offering you the tricks and tool of the CEO trade?

There are lots of consultants in the world. The trouble is finding the one who really fits with what you need. What to do? Start here:

  • Ask your advisors and industry colleagues for referrals (but not your investors or Board members – you want your own person).
  • Make certain the consultant has long and deep expertise in your industry.
  • Check the consultant’s background, website, social media, and testimonials.
  • Have a long first meeting, or two meetings (a 2nd meeting after you have checked the references).
  • Talk about colleagues you have in common, and the challenges they have faced.
  • Ask for success stories and failure stories.
  • Listen thoroughly.
  • Ask for references, and check every one, asking all the specific questions you might worry about (say, trust in confidentiality, availability of time, response in emergencies, loyalty, commitment, and weaknesses).
  • Have a 2nd meeting, asking the candidate all these questions directly that you have learned from the reference check.
  • If proceeding with a contract, set up a paid trial period of 30-60 days, during which either of you can walk away with no fault. If paying in both cash and stock, delay the stock vesting date until after the trial period.
  • If your consultant isn’t comfortable with this, look further.

I once told one of my best clients, “If you are not thrilled to speak with your consultant, or you don’t feel free to call her about anything that is concerning you, get another consultant.”

Having fulfilled this role with technology CEOs for more than 20 years, I have found this procedure to be the most fair for all the parties involved. And my best clients have always been the ones who understood that this advice and support was missing in the mix of their early stage efforts.