Greetings, manager!
Someone this week said “You’re very cutthroat aren’t you”. Ouch. It wasn’t great to hear, and honestly, it made me pause. Have I been swimming in the deep end of people problems for so long that I’ve forgotten the water is full of, well, people- not just neat little problems to be solved? It’s easy to want things black and white, especially when you’re under pressure, but humans are gloriously, frustratingly, wonderfully colourful. I’ve attempted in the last few weeks to make the grey feel more black and white, but I’ll revert to colour soon enough!
How far should loyalty take you?
I've got someone in my team who's been working for me for four years, and honestly, I've really grown to like them. They've done wonders for the business in the past, but we're in a different spot now, and the role- and frankly, their skillset for what we need now- isn't quite matching up. I'm stuck. I know I can't just brutally ‘exit’ them, especially with our history, but what on earth can I do? I feel like a terrible person even thinking about it.
Even writing this must have been hard, because I know that as a founder that cares (which you are, by nature of asking) this is a tough thing to be. The truth is- there are business sizes that suit different people- I’ve seen someone be the king of a team of 7 and flounder at 18, and vice versa.
It’s incredibly tough when friendship and loyalty feel like they’re clouding your professional judgment- or making the clear decision feel impossible. Here’s the thing, though: sometimes, a well-managed, compassionate exit can actually be the best path forward for everyone involved. Yes, really.
1) The off-the-record (but serious) chat. This is your starting point. Not an ambush, not a disciplinary- just a real, human conversation. Frame it around the future: "Let's talk about where the business is heading in the next 12-18 months, and what that means for roles and skills. And crucially, let's talk about what you envision for your future, and where your passions lie." (Or, go straight in with “Do you think this is still working?”).
2) Listen. Properly. You might be surprised. People are often more self-aware than we give them credit for. They might already be feeling the disconnect, wondering about their next step, or even feeling a bit bored or unchallenged if the role has outgrown them (or vice-versa). The conversation could go in a direction you totally didn't expect.
3) Explore alignment (or lack thereof). If their goals, skills, and the business’s future needs genuinely don’t align, that’s not a failure on anyone’s part- it’s a reality. The question then becomes: what’s the kindest, most constructive way to acknowledge that?
4) The graceful transition. If parting ways is the right move, then focus on supporting them in a kind and genuine way as they transition. This isn't about shoving them out the door. Can you offer outplacement support? Time off for interviews? A glowing reference for the brilliant work they did do? Can you help them network? Make it about setting them up for their next success, not just ending their time with you.
5) Legacy matters. Remember, their departure doesn't overshadow all the great work they’ve done. Acknowledge it, celebrate it. This is simply the next step in their journey and the company's evolution. Sometimes, the kindest thing you can do for someone is to help them find a place where they can truly shine again, even if it’s not with you.
It’s a hard road, but approaching it with honesty and compassion is key. You’ve got this.
How do I leave well?
I've been really loyal to the startup I work for- five years now, which feels like a lifetime in this world! I’ve learned so much, and I care about the team and the founder. But deep down, I know it's time for me to move on. I’m ready for a new challenge, maybe something a bit more established, or just… different. What's the kindest, least disruptive way to do that? I’m terrified of burning bridges, especially as founders talk.
First off, five years in a startup! Seriously, well done. That’s like dog years in career terms- you’ve probably lived through several lifetimes of pivots, late nights, and questionable office snacks. Give yourself a massive pat on the back for that commitment and journey.
Leaving can feel incredibly daunting, especially when you’ve poured so much of yourself into a place and built strong relationships. That fear of "what will they think?" or "will this mess things up for them?" is totally normal.
Here’s the good news:
1) It’s okay to go. Ultimately, no one should resent you for wanting to grow and move on. Good leaders understand that careers evolve. And honestly, for all you know, the founder might have sensed you were ready for a change, or perhaps the role itself was evolving in a way they knew might not be your long-term fit, but they didn't know how to broach it. These things are often more mutual than we think.
2) Focus on your next step. Before you even breathe a word, get clear on what you’re moving towards. Don’t just run from the current situation; run to an exciting new opportunity. This clarity will make the entire process feel more positive and purposeful for you. (And make sure you’re not just leaping from the frying pan into the fire- do your due diligence!).
3) The approach. When you’re ready, schedule a dedicated, private conversation with your founder/manager. Express your gratitude genuinely. Talk about what you’ve learned and valued. Then, explain clearly and calmly that you’ve decided it’s time for your next chapter.
4) The transition plan. Offer to make the transition as smooth as possible. A good notice period (and sticking to it professionally), thorough handover notes, offering to train your replacement if timing allows- these things go a long way. Show you’re committed to leaving things in good shape.
5) Keep those bridges strong. You’re right, industries can be small, and reputation is everything. Leave with grace, professionalism, and a genuine sense of appreciation. Stay in touch (LinkedIn is great for this) and be a positive ambassador for the company even after you’ve left.
Your next chapter awaits, and it’s bound to be an exciting one! They’ll miss you, for sure, but they’ll also (hopefully!) be cheering you on.
So, whether you’re wrestling with a cutthroat decision or trying to paint your own colourful next step, remember that kindness and clarity can go a long, long way. These things are never easy, but you’re not alone in navigating them. Keep those questions coming—the more colourful, the better!
P.S. PS Did you know that a fairy is born every time you forward this email? Okay. That’s a lie, but it does make me do a little happy jig.
Bee xoxo