strategic consultant to:  

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.

I’ve been watching my clients CEOs, their teams, and prospective CEOs make difficult decisions during the past couple of years, in these unfavorable economic times. Knowing most or all of the perspectives of the players (since everyone seems to tell me everything), I started an evolving list of questions to ask myself when deciding on important choices, like when to start something, or when to stop something, or when to take a risk, or how much of what to believe.

So here is the list I’ve been evolving:
1. What do I really want at this point in time re: this opportunity?
2. What am I willing to risk to have it?
3. How long can I sustain that risk?
4. If I cannot sustain the risk (say, twice as long as I would expect to), will I have taken all the risk for nothing? What would be my “lost opportunity” costs?
5. What other opportunities do I have, or might I have, if I did not move forward with this? Can I sustain the stress of “not knowing” about what may show up if I do not move forward on the opportunity at hand?
6. What do I really know about this? Who said it?
7. Do I trust who said it? Is this person in a position to actually know about this opportunity and its risks? Does he or she have an agenda (obvious or hidden) that has nothing to do with me?
8. Am I hearing facts (i.e., that can be verified?) or interpretations, or wishes & dreams & delusions? How can I investigate this?
9. Who else can I ask about this, who might have enough experience to guide my choice, and tell me what I have forgotten to consider?
10. What is the worst that can happen? Can I survive that consequence and continue on or start again, if the worst arrives?

Please send other questions you might ask yourself, to open a conversation about this.
And good luck.

I am often approached by entrepreneurs who want me to consult with them on their large visions of change that their skills and (to be developed) technologies can create. This is the spirit of entrepreneuring in its most original, and often lovely, form.

Still, the bond of reality must come to bear at some point, and I am often the bearer of that bond. So, I want to share here the initial questions we would address in the first couple of days of meetings together.

What life do you want? This means your life, your lifestyle, your financial condition, your partnering with someone in the business and/or at home, and so on. This is not a question about the business or vision you want to build. The venture should be built to support the life you want, or you will not sustain its long-term development.

What financial condition and life stage are you in? How much capital do you have to live on in your usual manner, to send the kids to college, to retire on, to be safe with? How much capital do you have to commit, (that is, to risk and possibly lose) to this new venture? How much reliable access do you have to outside capital in any form – friends and family, grants, angels, venture capitalists, debt collateral, and so on.

If the above answers lead you to build a venture, how should you begin so as to create a viable pathway to your larger vision? How many years ahead of the market (and its acceptance) is your vision? What part do you build first? How does the first part you build create the credibility and funding for the next part? What corporate structure is best suited to such a venture and its capitalization and effective outreach? What strategic alliances and capital might be available? And so on. This is a kind of venture roadmap which addresses capabilities, time to build, capital to build, time to market, time to ROI, and other issues. It informs and is informed by the issues of lifestyle and financial conditions already noted.

I try not to talk my clients out of their visions and dreams, although that does happen sometimes, and they are grateful for it. One told me, “That’s the best consulting money I ever spent – I could have risked everything without knowing those elements that will doom this idea.”

This kind of early risk-assessment of a new venture leads the entrepreneur to build what can be built as the stepping stone to building the larger vision. I told a client once, “This is a marvelous, large and needed vision. It is 10 years ahead of its time, needs $30M – $50M to just launch, and requires you to change the behavior of three major industries. You have just short of $1M in capital. So, take this vision, and come back to me with a single mosaic of that larger picture, a mosaic that would be critical to the first steps toward the vision, something we can build on the capital we have. And we will build that.” (and we did).

Often those with such large visions are first time entrepreneurs. Serial entrepreneurs know more clearly what it takes to build even a small idea. I point out that the mosaic will be the first business we build together, and then there can be another and another, and the entrepreneur will learn more about a company-building with each venture, while creating the larger vision step by step.

I also use this risk-assessment with established ventures that need to re-position their target markets, their international expansion, their response to new competition, or their new pricing configurations. And with my clients when they have exercised a successful exit and have new wealth, but still want to build the next new thing. The lifestyle issues are included only if the client has changed his or her life stage, wealth status or needs. My clients and I also use this risk-assessment during downturns to find their adjacent markets and new models for sustainable profitability.

I always think it is wise to stop for a couple of days and ask all the questions that should be asked, before venturing into new territories.

I always hear about the passion of the entrepreneur, and the dedication of the small business owner.  I am used to working alongside my CEO clients with long hours, late nights and an impassioned focus on the vision of the company.

But every once in a while, I am caught off guard by seeing this dedication in action when I’m not looking for it.

I was on a weekend holiday with my husband, hanging out in Monterey following a friend’s wedding in Big Sur.  We stopped in for supper at an authentic English pub.  It was the night of the Big Game (don’t ask me which Big Game) – and there was standing room only in both the bar and the adjoining dining room.  The hostess was an elegant small woman in a simple black dress, and she might have been the manager, as she was directing all this traffic and people, keeping a real smile on her face, and assuring us she would find us a seat.  We assured her the pub seats were fine, no need to wait on a place in the dining room to clear.  Of course, there were no seats in either, and folks three-deep standing at the bar cheering and booing.

We chatted with the locals a short while, when the hostess appeared, ducking under the arm of a couple of very tall men roaring their support for the home team.  She had found us a small table in the bar, and escorted us to it.  She was bubbly and friendly and I remember thinking she was an excellent choice as hostess, and how much her manager or boss must appreciate her.

After a hearty supper of Cottage Pie and a half pint of Taunton’s finest cider, while my husband was paying the barman, I slipped through the crowd (Big Game still ongoing) and found this excellent hostess, with a fiver in my hand.  I believe in tipping for excellent service, and she had provided it.

“I must say what excellent work you do,” I said, offering her the cash.

She laughed and said she couldn’t take it.  “Thank you so much,” she continued, “but I am the owner.”  And she beamed.  And I beamed. 

Behaving with impeccable manners is one of your strongest strategies. It builds and sustains your reputation, which as an entrepreneur or a consultant is your most valued asset. Your reputation precedes you in all new introductions, with prospective clients, and with existing clients and colleagues who speak of you.

There is great power in excellent manners. It allows folks to trust you. Those extra gestures of politeness are respected and welcomed in our too-fast world of 140 character communication. Sometimes a colleague won’t specifically understand why he or she thinks so highly of you, but will always hold you in high esteem, and say so.

Here are some of those gestures of good manners:

• Write a brief note of thanks following every initial meeting, even if you were not the one requesting it. This should be automatic and within 24 hours of the meeting.
• Acknowledge your client/prospect/colleague’s ideas, even if you will not participate in them.
• If you have pursued a prospect several times by follow-up email or voice-mail, but have received no response, send a closing note that acknowledges the conversation or meeting your shared, and say you will be available “whenever the time is best.”
• It is not weakness to be available, but graciousness. If you are not available later, you can say so then, with your kindest regrets.
• Do not expect others to have the good manners that you exhibit – impeccable behavior is more and more rare.
• Do not take others’ rudeness personally (it won’t help your situation nor change anyone’s behavior).
• Be generous with your advice, even if you have not signed on to the work. But don’t do the work itself before you have a contract.
• Be supportive of the idea, even if you doubt its ultimate success. How many times have you mis-judged the next new thing?
• Be polite: if you feel you must issue some warning about an idea, do it in positive terms, as a suggestion to safeguard against the unexpected.
• Take the time to share some bit of news, or an announcement of a potential competitor, or an article that may be useful. Do this with clients, colleagues, vendors, and prospects. This is part of your generosity – that you are thinking of someone and taking the time to show you remember them. Be simple about this – attach the information and just send a brief message with it, “thought of you and hope this is of interest.”
• Spend time with younger folks who seek your advice, even if they can not be clients or prospects. They will grow older and more advanced in their careers, and remember that you were kind to them. This includes teaching as well as one-on-one meetings.
• Listen more than you talk. Much more.

We live in an aggressive get-ahead world, filled with competition. Excellent manners are the inverse of this aggression – the yin, not the yang. There is great power in having so much abundance that you can share a note of thanks, an hour of your time without expectation of gain, a message with a piece of useful information for no reason other than to share it.  You will be remembered for these gestures.