Why you need an Executive Career Coach


You’ve got your golf handicap down below 5 – does that mean you never take another lesson? You’ve mastered your handstand and crane, but you still take yoga classes right? Even people who are very accomplished, who have succeeded to very high levels – even those people (particularly those people!) understand how important it is to be constantly evaluating progress, strategizing about direction, and getting objective support as they do so. But not just any objective support – when you’re at the top of your game you need top notch partners on your path. For senior level executives – accomplished, ambitious, growth-oriented leaders – one of the smartest alliances they maintain is with an executive career coach.


We think that most executives should have a career coach on stand-by. More specifically, an executive career coach – someone who understands the unique nuances, complexities and stakes involved in career moves at the executive level.

This is not a self-serving post (well, not entirely). We work with executives across a wide array of topics and issues, and we rarely sell our services specifically as coaches who focus on careers. Rather, career is always a topic that arises, and sometimes the topic that consumes a lot of our time together whether or not it was set as part of the agenda up front (and it usually isn’t).

Your career path needs regular attention and your career goals may need frequent tweaking. You always need to be ready to make a move or sell yourself into a new role, whether internally or externally.

At the senior levels of an organization there are few, if any, people with whom you can talk transparently about your career goals. Your peers are, or see themselves as, your competition internally. Your boss has a vested interest in your career following a particular trajectory, and your direct reports either fear the change a new boss would bring or have their own eye on your current role. No one is objective, and few if any represent a “safe” space for a career conversation. Enter the objective third party in the form of an executive coach.


An executive coach’s career conversations with senior level leaders can and do move from the tactical to the strategic and back.

At the tactical level we’ll want to ensure the executive is visible in all the important places (LinkedIn being the obvious one, as well as any industry and function-specific networks). We can act as an accountability partner for an executive who wants to – or has to – undertake an active job search. Some executive coaches have expertise writing resumes and bios, and most all experienced executive coaches are able to give feedback on those important marketing documents.

At the strategic level we create conversations and invite reflection about the alignment of career with life, how to frame and design a legacy, financial goals and succession issues. We challenge conventional or convenient assumptions. We encourage when needed, and celebrate at every opportunity (something most executives and high achievers could afford to do more often).


1) When you need one you’ll be too late. We regularly get inquiries from leaders who have just been approached about an opportunity and need assistance navigating the process – and too often we aren’t able to respond as quickly as they need support. Clients with whom we have – or have had – an active relationship can get usually get access to their coach on short notice if necessary.

2) You are always on display. Every bit of news coverage and PR, every LinkedIn profile and post, every mention by a competitor, every time a recruiter calls one of your past or current colleagues – the world is always watching. Having an expert in executive career management monitoring your presence and giving you feedback ensures you’ve got an objective perspective at work evaluating how you’re showing up in the world.

3) Career choices and inflection points don’t show up predictably. We’ve had calls from clients who thought they’d be staying in their roles for a few more years only to find that their organization had other ideas, necessitating a rethinking of their career plan under the pressure of time – never a good state of mind from which to be doing reflective thinking.

4) You’ll want to have answers if you’re asked about an opportunity. Having a clear sense of your path forward from your current role, as well as your long term professional and personal goals will help you be ready when presented with a new opportunity – whether internal or external.


There are many coaches who market themselves as “career coaches.” But for a senior level executive, a coach who can be helpful to you as you navigate your career journey should have some specific skills and qualifications. Here’s what to look for:

1) They are trained as a coach. Coaches ask questions, make objective observations, listen to you deeply and challenge your thinking. Lots of people are eager to give advice when it comes to careers – advice that is well-intentioned but that is coming from their own opinion and experience and therefore not based on your own interests. A trained coach will elicit your goals, fears and assumptions and support you crafting a path that is aligned with what’s important to you.

2) They’ve had their own successful career, ideally to the executive level. While we rarely give career advice, the perspective of having built a successful and progressive career and dealt with job search and career path questions is useful and ensures the coach is relatable in the context of a career coaching conversation.

3) You feel comfortable with them. Career discussions are deeply personal so fit or chemistry is important. You’re going to be sharing personal reflections and crafting important goals with this person, so you’re going to want to be sure you trust them.

4) It’s a bonus if your executive coach has expertise directly related to the process of job search and career path navigation. Not critical, but helpful in that you might be able to avoid shopping for additional services along the way.

On the Parachute Executive Coaching team we have a coach who was formerly an executive recruiter, a coach who used to be a senior HR leader, a coach who specializes in executive presence, and two coaches who have worked in executive career transition. These coaches bring unique and specific skills to their career coaching work. Reach out to us to discuss how we can add value to your career journey.