08/23/21

CEO Shoptalk – Executive Decision-making

One of the things that strikes new CEOs is how bloody many decisions there are to make to run a startup and a fledgling business to say nothing of one that survives the trip from the cradle to the marketplace.

I have read that a CEO makes more decisions in a day than CEOs did in prior times in a month — prior times being defined as pre-personal computer and Internet.

I was in business before the PC and the Internet and I totally agree with that assessment. No big surprise there, right?

Continue reading

06/1/21

CEO Shoptalk — You Will Learn

About five years ago, I had a chat with the younger brother of a successful CEO. The older brother was a friend of mine of longstanding and through him I met the younger brother.

The younger brother was in awe of his big brother — All State Basketball First Team kind of awe. We got to talking about his brother, the CEO/Founder, in that capacity. He was, admittedly, very good. Plus, he was a good guy with that aura of a winner that guys like that have.

“I could never do what he does,” said brother younger. “He just knows what to do. He’s a natural.” It was a serious lament, so I told him the following:

 1. No CEO/Founder ever knew everything he/she needed to know before they started the company even if it is their fifth company.

Continue reading

02/2/21

The Role of the CEO In Dispute Resolution

Several years ago, I was advising a fairly inexperienced CEO — a terminal condition that everybody eventually outgrows, remember that — who found himself in the midst of a dispute in the 8/10 range — meaning it would not tank the company, but it would change the speed, trajectory, and azimuth of the company’s future progress. It was important.

There was plenty of regrettable behavior on both sides and there was an important legal issue, but it was a heated and contentious confrontation made moreso by the personalities involved. These personalities were not the CEOs’, but the management of both companies.

Push led to shove and they were on the brink of paying off some lawyer’s lake house.

They had both talked to their lawyers, but no lawyers had been unleashed. It was still solvable.

Continue reading

01/18/21

Stopping To Find The Joy In The Storm

I recently had a Chairwoman of the Board client, one of my favorite clients (equally brilliant husband is a former client), cancel a meeting. She is a delight to work with so I miss it when she cancels.

Her reason was that it had snowed in Madrid and she had small children who needed to build a snowman as it did not ever snow in Madrid.

Actual Madrid snowman

[It ended up snowing more than three feet in Madrid, so if she hadn’t chosen that early moment to build a snowman, it would not have happened. As in life, timing is everything.]

Continue reading

01/4/21

The $10MM Gross Revenue Reality Check

If you are a startup, I hope one day soon you get to $10,000,000 in gross revenue. If you do, I have some thoughts for you.

A caveat first — there are a great number of exceptions to what I am going to share with you, so do not fall prey to missing the difference of your situation or embracing every word I say, but there are reasons big and small as to why I hold these views.

Continue reading

12/4/20

Planning In The Age Of COVID

If you are the CEO of a startup or small business, the months of November and December are when you must be planning what you will make happen in CY 2021 — and, yes, there will be a Calendar Year 2021 whether you plan for it or not.

You should be following a discipline something like this:

Review 2020 performance — review and discuss with your senior folks with an eye toward segregating the loser from the winners, the saints from the sinners

Based on 2020 performance, create your 2021 plan with input from your senior folks

After a careful review, publish the “preliminary” plan and sit down with your Board to get feedback

Revise the plan

Publish the plan

Brief the plan to the company and get buy in

This can take two weeks or six weeks. It should be started in November, finished in December, and published before Christmas. 

Continue reading

10/3/20

CEO Shoptalk — Hard Conversations — How?

If you are a CEO, you will have hard conversations with your people, board, investors, shareholders sooner or later. [Love a good cliche in the morning, no?]

The nature of the conversation isn’t really important. What is important is how you prepare for it.

Pro tip: The preparation for a hard conversation will have more impact on the outcome than the actual conversation because it will set the nature of the conversation.

Continue reading