By Howard Seidel, Senior Partner of the Essex Program at Keystone Partners 

Master executive career decision making with intentional strategies. Get expert guidance on career transition strategies and leadership planning.

Executives who are leaving, have left, or are thinking about leaving their current role for something else often find themselves at a career “inflection point”. What do I want to do next? Is this next potential opportunity the right opportunity? As an executive career coach who specializes in working with executives transitioning from a current role, in thinking through “what’s next,” I witness how difficult these decisions can often be. 

There are a variety of obstacles that make major career decisions difficult. First, most career decisions are made with imperfect information. What will it be really like to work for this company? Is this role better than one I am in or had? Is it better than the one I might find in another 3 months? What is it that I really want to do? Career choices are a great example of decision-making under uncertainty. We must make our choices with finite information and make what are hopefully “educated” predictions of potential future outcomes. 

We also often face competing career priorities. For example, an opportunity may represent the right money and intellectual challenge but the culture and lifestyle it presents is not ideal. If so, what are we willing to compromise on, and if so, by how much? 

Additionally, career decisions are often wrapped in what I think of as psychological “noise”. I occasionally hear my clients talking about a career choice they “should” make as if it’s some type of obligation, rather than a want or a need. One executive, in his late 50’s initially remarked to me that while some type of “active retirement” was appealing and financially feasible “my father worked until he was 70, why shouldn’t I?”. There was a sense of guilt attached to a decision to do otherwise. 

Another potential obstacle is fear. Sometimes clients look seriously to take a job they find quickly even though it’s not really what they want, because it is the “bird in the hand”. What if nothing better comes along soon? Or alternatively, a quick career decision, even if less than optimal, will allow them to bypass their fears about the discomfort of a full job search process (along with a possible dread of “networking”). 

Or someone may in their interest to accept a new opportunity disregard certain warning flags that were always there but that they didn’t fully consider until after it was too late. I sometimes meet a new client who after departing from a situation that quickly proved to be a bad fit says to me “I should have seen the signs”. Additionally, sometimes an executive can get seduced by one aspect of an opportunity such that they overlook their other priorities. The money, or the prestige of a role, is so great, they ignore other important wants. Additionally, someone may get locked into a previous set of priorities not fully coming to terms that their career values have changed. As a recent client opined to me, I no longer need to make the money I used to make, but it’s hard to accept that a reduction in salary for even a job I will love is not some kind of career backsliding or ego hit. 

So how to make the best career decisions with imperfect information and this underlying psychological noise? For me it is all about fostering a strong sense of intentionality. Decisions cannot be made under perfect conditions, but the aim is to work towards the most informed decisions one can make, becoming as aware as possible of both the external and internal factors that can weigh into one’s choice.

In my view, that means focusing on the following things. 

1. Distinguish between career “shoulds”, “wants” and “needs”. If something is a should as opposed to a want, what does that mean? If something is a need, why is it a need? What would be the consequence of not getting it? 
   

2. Assess and understand your current professional priorities. Not what was important to you 10 or 20 years ago but what things are important to you today. Maybe some of those things are the same but it is important to consider any changes rather than go on psychological autopilot making decisions on old priorities. 
   

3. Assess new opportunities in terms of your current career priorities. Waldroop and Butler of Harvard Business School identified 13 career personal professional values including such things as the intellectual engagement of a role, cultural fit, money, career positioning, lifestyle, etc. I recommend clients identify the 5 or 6 things most important to them for their professional life and then use each value as a criterion for evaluating potential opportunities (on a 1-10 scale with 10 being ideal for that criterion). 
   
   To be clear, the aim here is not to completely remove “gut reactions” from the decision-making equation. The objective is to couple gut instincts with an analytic approach to decision-making to avoid the kind of psychological noise elements mentioned above. If at the end of the day an executive makes with full awareness the decision to ignore all other priorities except one, that is his or her choice. But at least it is a very intentional choice. 
   

4. Recognize any warning signs and don’t ignore them. For example, what if in the role as offered, you’d be the 3rd CFO within a 2-year period. Maybe that makes sense given the context, but it’s worth exploring. Assess any flags that come up; don’t just wish them away. 
   

5. Weigh risks on both sides of a decision. It’s easy to worry about the consequences if you decide not to accept a job. But sometimes folks do less thinking about the consequences on the other side of the decision – what if you take the wrong job? Will it hurt your reputation? If you leave, will it be hard to explain? Will I be signing a non-compete that will limit my future options if this proves to be the wrong fit? 
   

6. Get as much information on an opportunity as possible. Do your research on organizations and the people with whom you will be working (especially bosses and peers) via all available means including personal contacts. Distinguish objective data from advice. Both have value but advice, though generally well meaning, often comes from the framework of the person giving it. Apply any advice to what’s important to you.
   
   I am generally a big believer in the idea that in any job interviewing process, you “sell first and buy later”. By that I mean the first objective is to prioritize having organizations see what value you can bring to the organization to improve the chances of receiving an offer. The more they see that value, the more leverage you have in subsequent negotiations on salary and other requests. But in addition to the information you pick up about an organization in the normal course of interviews, (including what you learn about its financial health, business prospects, and its culture), getting an offer changes the power dynamics in a search process. Now is the time to ask the more difficult questions that you believe need answering before you can accept. 
   
   Major career decisions can be hard. There are so many variables to assess, and the accuracy of some of those assessments can’t be fully understood in the present. Perfection in career decision-making is a lofty but hard to achieve desire; informed and intentional decision making however, should be the goal. 

How Keystone Partners’ Essex Program Supports Executive Decision Making 

At the Essex program by Keystone Partners, our executive transition services work exclusively with senior executives navigating these complex career crossroads. Since 1998, the Essex program has provided sophisticated guidance that goes beyond standard outplacement, offering unlimited access to senior-level consultants who understand your executive experience. 

Whether you’re exploring traditional C-suite opportunities, board governance roles, entrepreneurship, or portfolio careers that balance multiple interests, Essex provides the strategic transition planning and market intelligence you need to make truly intentional decisions. Our approach includes guidance through all options – from traditional executive roles to active retirement – with the industry’s lowest client-to-consultant ratio ensuring personalized attention to your unique situation. 

When your career reaches an unexpected crossroads, you deserve more than ordinary guidance. Request Keystone Partners’ Essex by name to explore how our executive transition services can support your next intentional career move.