The right time to hire an executive coach is when you can name a specific outcome and you find yourself in one of three seasons: you are stuck and cannot figure out why, you want to accelerate toward your next level faster than you can on your own, or you are stepping into a role you have never done before. If you are simply coasting or cannot point to a clear outcome you are chasing, you probably do not need a coach right now.
I gave a keynote last week, and right afterward someone walked up and asked me a question I hear all the time… “When is the right time to hire an executive coach? Do I even need one?”
It’s a fair question, and my answer is probably a little contrarian compared to what a lot of coaches will tell you.
For most of my life, I was the introverted IT guy, head down, convinced I could grind through anything on my own. My mindset was always the same… “I’m smart, I’ll figure it out, I don’t need anybody’s help.”
Then about ten years ago, I jumped in to lead human resources, and I walked into a team full of bubbly, extroverted, outgoing HR professionals. I had no idea what I’d gotten myself into…
That was the first time in my career I got intentional about finding a mentor and actually engaging an executive coach. Looking back, that decision became a real turning point for me.
How Long Should You Work With an Executive Coach?
Here’s where I tend to differ from a lot of folks in this space. Plenty of coaches will try to lock you into a one, two, or even multi-year agreement, and the pitch is almost always the same… “Real change takes time.”
There’s some truth to that, but if a coach truly knows what they’re doing and knows how to get you where you want to go, it shouldn’t take years. I was at another event a few months back where someone stood up and proudly shared that they’d had the same coach for 17 years, and I’ll be honest with you… at that point, that’s not really coaching anymore. That’s therapy, or a thought partner, or a strategic advisor to bounce ideas off of. Those things matter, I just wouldn’t call it coaching.
The way I see it, here are the times you should seriously consider this.
When You’re Stuck in the Same Role for Years
The first season is when you’re stuck. You’ve been in the same role, the same seat, year after year, and you know deep down you’re capable of more, you just can’t quite put your finger on what’s holding you back.
Your boss, your friends, your family… they all keep telling you to keep crushing it, keep working hard, you’ll get there eventually. As time goes on, though, you start thinking there has to be a better way.
That’s the moment to raise your hand, because it can’t just be work, work, work, and hope that someday somebody finally recognizes your value. The highest performers in the world don’t operate that way… when they get stuck, they bring somebody in to help them see what they can’t see on their own.
If you’re stuck, stop being stuck. Reach out, and you will find somebody who can help get you to that next level.
When You Want to Reach the Next Level Faster
The second season is acceleration. You’re already on a decent path, things are working, but you want to compress the time it takes to reach that next level.
Some seasons of life we’re coasting, and that’s completely okay. Other seasons we want to drop a gear and start making real, meaningful progress.
Can you grind your way there on your own? Of course you can, but if you step onto a racetrack you’ve never driven before, it helps to have somebody in the passenger seat calling out the turns, calling out the speeds, helping you navigate so you reach the finish line faster.
When You’re Stepping Into a New Executive Role
The third is what I call a step change transition, and it’s when you step into something you’ve never done before… maybe you just got promoted into a VP-level role, or somebody handed you the reins to a department you’ve never run.
This is when you absolutely need to consider finding someone who has actually done it before. “How I Went from Director to VP”
The coach I hired when I took over HR had a deep background in human resources, and they helped me understand behavioral styles, employment law, benefits, payroll… all the things I didn’t even know I didn’t know.
Could I have figured it out on my own? Sure, eventually, but working with somebody accelerated how fast I became proficient.
I did this again and again over the years… when I was asked to start an ESG function, when I stepped in to lead safety and transportation, and most recently when I jumped into entrepreneurship.
I walked in thinking, “Sean, you’ve been through 48 acquisitions and two IPOs, you know how to scale a business.”
Then reality hit… I had no clue how to start one. I didn’t know what a sales cycle was, or a CRM, or how to move someone through a pipeline, so I found people who did.
Here’s the pattern: every time you step into something new, you usually got there because you were great at the thing you used to do, and that does not automatically mean you’ll be great at the new thing. You can learn it, absolutely, but the right person helps you get there so much faster.
When You Don’t Need an Executive Coach
If you’ve achieved big things and you’re in a season where you just want to coast and enjoy the fruits of your labor… then enjoy it, you don’t need to hire anybody right now.
When you can’t name a specific outcome, that’s another sign to hold off. “I really like this guy Sean, he’s motivational and seems to know his stuff” is not a reason to hire me.
If you can’t point to a clear outcome you’re chasing, save your money, save your energy, and just enjoy that season of your life.
How to Choose the Right Executive Coach
If you do decide it’s time, the next question is how you find the right person. This part got murky during the pandemic. Half the world lost their jobs, and half of those people came out the other side as executive coaches… a lot of them HR managers who picked up a coaching certification. They’re wonderful with people, truly, but that’s not the same as having lived the outcome you’re chasing.
The best filter is actually pretty simple. Look at the results that coach has achieved, and ask yourself… are those the things I want to accomplish? If you want to expand your role, ascend into the C-suite, or navigate a merger or an IPO, find somebody who has actually done those things, and if they can’t show you real social proof, treat that as a red flag.
When you finally get them on the phone, pay close attention to the questions they ask. A great coach asks the kind of questions that make you stop and think, “Wow, I’ve never even considered that before,” and that’s usually how you know they’ve actually walked the path.
Then do your homework. Interview as many as you can, look at their websites, their social media, their reviews. If one coach has three five-star reviews and another has almost 150, that’s a signal… not absolute, but a signal worth paying attention to.
One last thing on this… before you ever start, make sure there’s a clear, defined outcome. If your first session or two isn’t spent mapping out exactly what you want to accomplish, that’s a red flag too.
In reality, you should have most of that mapped out before you even begin.
Questions to Ask Before Hiring an Executive Coach
- Am I in one of these seasons right now… stuck, accelerating, or stepping into something completely new?
- What is the specific outcome I actually want to achieve, and have I written it down?
- Is this coach truly qualified to get me where I want to go?
Can you achieve great things without somebody in your corner? Yes, you can.
Will you get there faster with the right person beside you? Also yes.
Ready to Find Out If It’s Your Season?
If you’re in one of these seasons right now and you can name the outcome you’re after, that’s exactly the work we do at Wolf Executives. Executive advocacy means having someone in your corner who has actually walked the path and is invested in getting you there faster. Book a discovery call. Let’s figure out whether this is the right season for you.
Frequently Asked Questions
When should you hire an executive coach?
Hire an executive coach when you can name a specific outcome and you are in one of three seasons: you are stuck and cannot figure out why, you are trying to accelerate toward your next level faster than you can alone, or you are stepping into a role you have never done before.
Do you really need an executive coach?
Not always. You can reach big goals on your own through grind and trial and error. A coach is worth it when you want to get there faster, or when you are moving into something unfamiliar and want someone who has already done it to shorten the learning curve.
How long should you work with an executive coach?
Coaching should happen in focused sprints, not open-ended multi-year agreements. If a coach genuinely knows how to get you where you want to go, the engagement should be built around a clear outcome and timeline rather than dragging on indefinitely.
How do you choose the right executive coach?
Look at the results the coach has actually achieved and ask whether those are the outcomes you want. Favor proven social proof, pay attention to whether they ask thought-provoking questions, interview several, and make sure you agree on a clear, defined outcome before you start.
When should you not hire an executive coach?
Skip it if you are in a season where you simply want to coast and enjoy what you have built, or if you cannot name a specific outcome you are chasing. Without a clear goal, coaching becomes a waste of money, time, and energy.
About the Author
Sean Barnes is the founder of Wolf Executives and an executive coach and keynote speaker based in Houston, Texas. Over roughly two decades of progressive leadership, he led teams across IT, human resources, the project management office, ESG, and safety and transportation, and guided organizations through 48 acquisitions and integrations and two IPOs. He started his career as an introverted IT leader before stepping into broader executive roles, and today he helps directors and senior leaders build executive presence, expand their influence, and make the leap to the vice president level and beyond.
