Best Advice – How to access your next leader


On objective measures, leaders can be easy to vet. Subjectively, I suggest one diligence question that trumps them all…

We talk and read a lot about professional values…Values that range from exceptional and humane performance to basic and simple ethics.

In many cases, it is just that: Talk and writing. Just like the platform I’m standing onright now, it’s far too easy these days to publish a bullet point list of things you thinkothers should do.

This article is for those who expect it to be more than words.

Leader evaluation…Some background

Having been a part of a few organizations that are styled more as talent markets–professional firms that dynamically mix management and subordinate talent into short term teams–than as classical hierarchical organizations, I’ve gained a point of view on leadership evaluation that is perhaps helpful to those who have spent their lives living in the lines and boxes world of static organizations.

One of the benefits of firms styled as talent markets is that people–particularly junior people–get to vote with their feet. They learn that working with a bad manager is not a bitter pill they have to swallow for career advancement.

Bad managers and leaders are weeded out either through formal processes (surveys, 360s, and feedback), or simply through word of mouth.

Another of the benefits is that people actually learn to do their due diligence on a leader. They learn to ask about style and substance in polite but penetrating ways, and to judge the reaction accordingly.

Most corporate environments operating with a hierarchical organization lack this component of “churn.” And, that can be a good thing. People become masters of their work more readily.

But, those same people can also become resigned to their own fate.

In a corporate environment, the vast majority of a person’s job satisfaction is based on the leader/manager/supervisor they work for. That can range from the CEO to a front-line supervisor leading a work team.

So, when considering a new job, a transfer, or a new company, employing some talent market-style due diligence tips can help you avoid a bad experience that can last a very long time.

The diligence list…

First, the basics of leader evaluation. All of us should investigate basic performance and ethical values before joining a new leader.

Ideally, we do it with a mix of people who currently work with the leader, and who have previously worked with the leader.

In today’s world, it’s very easy to track down a few people who have close knowledge of an individual leader through prior interaction.

Some of the basic questions to ask include the following:

Does the leader perform?Is the leader accountable to others?Does the leader develop people?What’s the leader’s style in conflict?How does the leader handle competing factions?How does the leader manage big and small things?What is the leader’s track record of advancing peoples’ careers?How does the leader engender trust?Is the leader a clear thinker and direct communicator?

These are all “good” questions that anyone considering a new job should ask.

But they all leave out the litmus test of leadership: The re-buy.

That’s where my best advice comes in.

The kicker…One question to rule them all…

Here is the critical question. You might say I’ve buried the lead in this one, because it really is the one that matters.

The question you should consider asking when evaluating a new boss is this:

Would you want your son or daughter to work for this leader?

That’s it. That’s the simple question.


It creates emotional distance for the person answering it: They don’t have to admit they are an idiot for choosing or staying in a bad situation directly. They get an ego “out” by being able to say how different their situation is than what they would want for others.

It overcomes the endowment effect that we all suffer from when evaluating our current circumstances: We value where we are right now more than we would value it if had a clean slate to choose from. It’s a proven psychological fact. We make excuses for why we stay with our bad leader.

It gets to a fundamental question of humane values: A lot of people will walk through fire to provide for their families, and they will make every excuse and fully martyr themselves on their way to it.


When you ask them if they would put their kids through it, it gets personal and protective.

Most people look for better lives for their kids; not lives lived making up for bad leadership.

How to use the responses

Listen for the nuance in the response.

A lot of leader diligence is about the meta knowledge you will gain. The more senior you are, the more politically savvy the respondent, the more you have to listen.

Namely, if people cannot answer your questions or will not offer a reference, you should wonder why. It tells you something if a person, particularly a very senior person, refuses to give a perspective on prior leaders.

In that case, keep asking others who have been on the path.

One caution: You can always, of course, ask the question about whether a reference would work with the leader again; but remember that chemistry matters. Sometimes people leave for good reasons that don’t have to do with bad leadership.

A parting thought:

I’ve used this sort of litmus test question in countless diligence discussions; and it has been used on me in even more of them. I view both of those things as a good thing.

I’ve gone against poor “mood music” on this sort of question in only a couple of instances.

Knowing the outcome of those choices, I can only say:

Take my best advice.

Geoff Wilson is a strategy executive focused on the articulation of practical strategic principles for leadership and performance. If you follow people on Twitter, you might consider following him: @GeoffTWilson