Strategic Planning: The Executive Interview Process

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Whenever we’re asked by a client to help with strategic planning, we always begin with the same initial step:  comprehensive, one-on-one, confidential interviews of the company’s leadership team – namely, the CEO and his or her direct reports.

There’s a simple reason for this:  As a first step in establishing the context for planning we want to know where they stand on the company, its environment, its challenges, its future as well as themselves as a leadership team.  Just as importantly, since achieving leadership consensus is arguably the entire purpose of strategic planning, establishing a “baseline,” via interviews, as to how aligned or unaligned executives are to begin with allows us to assess just how difficult it’s going to be to bring them together on a final plan.  Consequently, interviews are an indispensable first step that we simply would never do without.

Here, in brief, are a few of the major areas we probe in these all-important interview sessions:

Prospects for Success?

Asking executives for their assessment of the prospects for success of the planning process on which they’re about to embark can be very revealing.  Consider the difference between a team that’s enthusiastic and positive and one that communicates a sense of resigned inevitability.  In either case, these attitudes need to be factored into how one approaches planning.

State of the Company?

We always ask executives to imagine they’re delivering a speech about their company that’s analogous to the President’s “State of the Union” address.  And we ask them to characterize the Company in a word, or phrase or brief sentence.  From experience, we’ve found this is a great way to distill very quickly not only the current state of things, but where each executive “lines up” on that current state.

 Company Direction & Mission, Vision & Values?

Peeling the onion further, we ask them how they feel about the “direction” in which the company’s headed “right now.”  In addition, we ask them to define for us the Mission, Vision and Core Values of their company.

This battery of questions never fails to be revealing.  There’s a world of difference between an organization where executives reply with the same, strongly-held answers and one where respondents fish for words that are clearly not “live” concepts or can’t recall what these concepts are, or worst of all, have not decided some of these questions for their company.  Either way, once again the implications of the answers begin to suggest the kind of planning process that we can anticipate and plan for.


Of course, as with any planning process, we get executives’ “takes” on the company’s “Strengths,” “Weaknesses,” “Opportunities,” and “Threats.”  Answers to these questions not only yield important background data, but they also enable us to gauge executive alignment.


We always ask executives to give us a few adjectives that describe the company’s culture.  Organizational culture is revealing in a myriad of ways.  Since it describes “how we do things around here,” it’s a good indicator of the norms and practices that the planning process will have to accommodate.  In addition, we ask respondents whether they think their culture is “conducive to” or a “barrier to” the company’s continued future success.  Since strategic planning is all about the future, getting a read on organizational culture tells us whether this client is likely to achieve its goals with incremental change or will need to be more transformative.

Leadership Team Process and Dynamics?

Asking a group of leaders about the history of their own interaction and group dynamics is the best way we know of to get a preview of what they’ll be like to work with as a group.  So we ask them how they’d describe their own meetings, their decision-making process, and how effective and efficient they believe them to be.  We ask them to rate the degree of trust that exists within the team, to assess the effectiveness of the way they handle conflict and confrontation, and so on.

Given the nature of the C-suite and the individuals who populate it, we find that these kinds of questions are often difficult to raise and discuss within the leadership group itself.  But an outside, neutral third-party can do so easily, while preserving anonymity.

 CEO Feedback

Lastly, it truly is “lonely at the top,” and typically, CEO’s have precious few, if any, opportunities to get candid, unadulterated, constructive feedback.  We cover that delicate territory by concluding our interviews with a number of questions about the degree to which the CEO establishes clear goals and priorities, encourages open dissent, makes clear decisions, keeps the leadership team informed, etc.  In our experience, senior teams take these questions seriously, and CEO’s, to whom we provide this feedback privately, invariably greatly welcome it.

Two-Way Value

Of course, the kind of interview process we’ve described here, happening as it does at the very beginning of the client relationship, is invaluable in helping us, as consultants, to quickly “get up to speed” on the issues and individuals involved.  But since we report out the key data anonymously at relevant points in the planning process, we can attest to how beneficial interview results are for our clients as well.  Given the sensitivities and power issues at play at leadership levels in any business organization, many of these issues would perhaps never otherwise have been raised – let alone dealt with – in an open, constructive way.

Here is what just one of our CEO clients wrote to us about the value of executive interview insights to him, his leadership team and his company:

“First, my top-line statement would be that I gained valuable insights that encouraged me to change my style and approach to leading the company.  This began . . . with your very successful one-on-one interview sessions in preparation for the Strategic Planning Conferences themselves.  At the time of the interviews, we were going through some unique challenges, and people needed and welcomed an opportunity to ‘go to confession.’  For our executives, these interviews were a good opportunity.  People realized they could trust you in that you were true to your assurances that you would maintain confidentiality.  For me, and for all of us, your summaries of the key themes of those interviews provided new and valuable insights.”

                                                                                                                                                                       — CEO, Strategic Planning Client

Obviously this engagement turned out to be a win for our client and, as a result, a win for us.  But it all began with a candid, authentic, confidential executive interview process that asked the critical questions of every member of the company’s leadership team.  This interview process has proven time and again to be a fool-proof first step for us, and we’re confident, if you try it, it will work for your strategic planning process too.