“I’m a mid-level leader at my company and really unhappy. How do you know when to quit your job, when so many others depend on you?”
That’s not an easy question, but it’s one of many we’ve heard before.
In the process of growing Lighthouse and writing this blog, we have talked to a lot of leaders. Often, they share a challenge their facing. Many of our posts are inspired by those conversations.
A number of managers have asked us forms of this question; what do you do when you’re deeply unhappy in a job, and you’re a senior leader?
Today we tackle that question, and how to transition out in a way that’s good for your career, and the company you’re leaving.
When do you make a change?
When you’re an individual contributor, if you’re unhappy for too long, it’s easy to just go get another job. You give your notice, help find and train your replacement, and all is well.
For better and for worse, when you rise in an organization, the stakes are much higher. While normally this is a good thing (more responsibility, compensation, and ownership), it has major drawbacks if you want to quit your job:
- Will your team feel betrayed if you leave?
- Will your team leave with you, creating a giant hole in the company?
- Are you breaking a promise you made to the leader that hired you?
- Will your departure hurt the company with customers or investors?
- Are you sending the wrong message to future employers that you can’t fix problems?
It’s not always fair, but that’s part of the deal of becoming a leader with more and more responsibility.
Staying isn’t always the right choice, either.
Even if you’re willing to “grin and bear it,” or sticking with it because of some of the aforementioned concerns, that may not be a good choice, either.
Being an unhappy manager has a significant impact on those around you.
Gallup calls this the Cascade effect:
How you feel absolutely will trickle down to the team below you, affecting their morale and engagement.
Whether you stay or go, being unhappy as a manager is no place to be. You’re affecting your team either way.
Quite the rock and a hard place!
When to Quit Your Job, if You’re a Leader (+ how to exit well)
Knowing what a difficult choice it can be whether you stay or not, we want to help you with this.
- Crowley is the author of Lead from the Heart and was a senior leader in the world of finance before that. You’ll see in his answer below how leading from the heart influences his advice on this tough decision.
- Fournier is the author of The Manager’s Path and was CTO of Rent the Runway. You’ll find the same direct, structured advice that is throughout her book we recently wrote about.
If you’re having a hard time in your leadership role, these answers can help you think about what’s best for you, your team, and the company you’re working for. Deciding when to quit your job is a deeply thoughtful process, like these responses.
Here’s what Mark Crowley advises on when to quit your job as a leader (and how to leave well):
“I may be old-school, but I still very much value employee loyalty, and see it as a sign of a person’s immaturity or selfishness when their resumé reflects a lot of moving around.
Shakespeare said “past is prologue,” and someone who hasn’t stayed working for any one company very long is all but shouting they won’t likely stay with you for any meaningful amount of time either. I’m not inclined to hire someone who hasn’t proved an inclination to be resilient, persistent and committed at their previous jobs.
As someone who values loyal people, I have always been one to show loyalty back. If I’m treated well, given opportunities to grow and to do meaningful work — and to work for an organization whose values I respect — I’m personally inclined to stay on and grow roots there.”
“But there are two primary reasons where my leaving a company would make sense — while still aligning to these values.
The first would be if the company changed in some way, or if I was given a boss who treated me disrespectfully, or failed to support my needs in important ways.
We’ve all had bad bosses, so I’m not speaking about running away at the first sign things aren’t working well. But if the organization moves in a significantly different direction, or if my boss can’t demonstrate that they value me and want me to stay — well, those are clear reasons to evaluate your options.
The other reason for leaving, of course, is when someone recruits you for an opportunity that’s just too great for you to pass up.
Leaving, in these instances, has little to do with the current company, and far more to do with a chance to do work that really challenges you and makes your heart sing.”
Resign the right way.
“Under any circumstances, I’m also old-school in the way I would resign. I’d offer more than two weeks notice if it helped the firm I was leaving transition more successfully. And I’d thoroughly explain to my employees all the reasons I chose to go.
I believe we build our reputation with each and every action we take in life.
Leaving a company on the best of terms isn’t just an indication of a someone’s character, it’s a sign they were grateful for all the opportunities that company gave them, and that they chose to honor that all the way to the end.
I’d rather a company feel they lost something when I left, than to have my final few weeks unnecessarily sully how I’m remembered there. So even if I’m not treated well those final days, my doing the right thing has always felt best.”
– Mark C. Crowley is the author of Lead From The Heart: Transformational Leadership For The 21st Century. You can connect with him on LinkedIn here.
Here’s what Camille Fournier advises on when to quit your job as a leader, and how to leave well:
“The decision to leave a company when you are in a senior leadership position is usually a pretty agonizing one.
I think the short answer is that, if you want to put yourself in the position of being able to leave gracefully, you need to have a successor in mind.”
Succession planning is key.
“There is a reason that bigger companies push their senior leaders to think about succession planning. You may need to groom people for months or years to get them ready to take over your job.
If you haven’t been working on teaching those skills to your potential successors, there is no way to leave without causing disruption.
It’s pretty common in tech for startups to try to hire externally to replace leaders as they go. This works sometimes, but more often it causes massive cultural clashes and a lot of attrition as the external person changes the shape of the team and often brings in some of their own people.
So if you truly care about leaving your team in the best place possible, make the case for why someone who reports to you now can take over your job when you leave.”
“Make sure they have the right relationship with other senior leaders, and have had a chance to show their own independent leadership. This is I think one of the best ways to set your team up for success when you leave.
If there’s no one who reports to you who is ready, you can offer to help with the search for your replacement. Depending on your relationship with the CEO and other execs, this may or may not work out, but it’s worth a shot.
What else should you think about?
Well, I think that it is a good idea to give a longer period of notice. Nothing burns bridges like a senior executive leaving with 2 weeks notice. Even with a replacement ready to go, the knowledge transition alone takes a long time.
I gave a long notice period when I left my last job, and while it was incredibly hard being a lame duck for that period of time, I still believe that it was the right thing for my team.”
But should you leave at all?
“Finally, there’s the question of deciding to leave in the first place.
Senior leadership is a hard job. It requires the stamina to deal with a lot of painful setbacks, interpersonal challenges, and stressful decisions.
But that doesn’t mean that you have to let yourself get burned out completely.
Make a point of regularly checking in with yourself on how you are feeling about work, and let that guide you.
If you spend 3, 6, 9 months miserable on a regular basis due to your job, you are risking burnout. Once you’ve gone to the point of burnout, it’s hard to bounce back without taking some time off work completely. Your team deserves a leader who can give them the right positive attention and energy.”
-Camille Fournier is the author of The Manager’s Path: A Guide for Tech Leaders Navigating Growth & Change. You can follow her on Twitter here.
Choose when to quit your job wisely.
Deciding to leave is never an easy decision. How you handle it can define your career.
Done well, you’ll have references and loyal team members. Handled poorly, you can burn bridges and ruin otherwise great working relationships.
If you’re thoughtful about the process, and work hard on your transition, you can avoid many of the biggest pitfalls. Take Camille’s and Mark’s advice when to quit your job as a starting point when you face this crossroads.
What advice do you have for leaders on when to quit your job, and how to do it well? What lessons have you learned in your career?
Make things better for your team.
Always remember what Andy Grove said. No matter what’s going on around you, you can make things better for your team.
With a few of the right habits, you can help them grow, feel heard, and perform at a high level. And you can do these regardless of what’s happening around you.
Whether you’re in a difficult situation, or simply want to do better taking care of your people with the time you have, you should sign up for a free trial of Lighthouse here.
Built with the best practices, helpful nudges, and the easy structure you need as a busy leader, it can make all the difference for you and your team. Learn more and sign up now for your free, 21 day here.