The Gift of Honest Conversations: Making Transitions Work
Summary:
Letting someone go is never easy, but avoiding it usually makes things worse for everyone. Here's a practical, human-centered approach to handling necessary transitions, one that maintains dignity, offers real choices, and often preserves relationships. It's about treating folks like the humans they are while still doing what's needed for your organization.
What’s in it for you:
You've been putting off a necessary conversation and need a better way forward
You want to handle transitions professionally without burning bridges
You're looking for language that's both clear and compassionate
You need a framework that honors both people and mission
Important note: I am not a lawyer or HR professional. This is not legal or HR advice - it's an approach I've found helpful over many years of leading teams. Always, always, always(!) consult with appropriate legal and HR professionals before having these conversations.
Helia’s Perspective
Oh how I wish I'd learned this earlier in my career! Transitions are normal, healthy, and often the best thing for everyone involved. The key isn't whether or not to make changes - it's HOW to approach them.
I learned this the hard way at Revolution Foods, where we restructured and did layoffs literally almost every calendar year. This was really hard, especially in years when I felt I had done exceptional work: 90+ customer retention, hitting sales goals, retaining our teams - none of which we consistently did at Rev in a fast growth/tricky industry with AMBITIOUS goals and an incredibly challenging ops model! -Changes were often made without even asking me!
But you know what? It also taught me something crucial: the importance of a business being able to do what was needed. Having the flexibility to change based on what we were learning and who was on the team was SO important to being able to do the work. It taught me that our work was why we were there, not to employ people. AND that how you did this made LOTS AND LOTS of difference.
Stumbling across Netflix's original culture deck for the first time offered a template for a different way of approaching things. They made decisions about employee fit that were rooted in business needs , but they did it with refreshing candor and generous severance. That felt like getting closer to something that worked.
The idea of bringing folks in, having honest conversations, and treating people like I want to be treated just kept evolving. There are times you need to decide and make the decision for people, and there are times when you can leave it up to the human - because we are all HUMAN!
When it came to making decisions about whether it was time for someone to transition from our team, I used to get stuck on how I - or the organization as a whole - was failing. I refused to give up. I felt a sense of possibility if we could just try a different way and ended up spending wild amounts of time focusing on specific employees. I was scared of making the tough call.This only prolonged the inevitable while creating unnecessary stress for everyone involved. And it pulled my focus away from carrying out the work our team set out to do.
My gut feeling was right and deserved to be trusted. The reality is - the impacts of me ruminating or trying to fix what couldn't be fixed rippled across the entire team:
The person in the wrong role isn't thriving, which feels terrible
The manager is spending a disproportionate amount of time trying to make things work OR avoiding the problem
The team feels the friction of misalignment
Each person involved - all of us - is feeling frustration, uncertainty, angst, and perhaps blame, insecurity, or resentment.
It was a painfully hard lesson for me to learn. Here's how I've learned to adjust:
My grandmother (one of the few times she met my kiddos!) was the most beautiful truth teller, bringing heart and honesty to each and every conversation. She inspires me to want to bring that same to every relationship I get to have, at work and beyond.
What this Looks Like in Practice
-
The first and most important thing for any organization is getting clear on your purpose. Are you trying to maximize profit? Be in the most places and help the most people? Change how a system operates? Employ the most humans or the same folks for a long time?
Once you're clear on the purpose you're trying to fulfill with your company, this becomes a grounding force for how you think about transitions.
I've never worked somewhere where building up a workforce of long-term employees was the primary goal. My work has always focused on driving impact, changing systems, achieving profitability(!), and expanding reach. Within that context, I spent too many days - sometimes even years! - knowing someone wasn't a fit but being too nervous to do anything about it. Getting clear on your mission helps cut through that paralysis.
-
When you have that gnawing feeling something isn't working, start by asking yourself:
Have I been clear about the company's expectations?
Have I asked this person what they need and want?
Am I meeting these needs and wants? Why or why not?
Sometimes addressing these questions solves the problem. I've seen seemingly insurmountable issues resolved through better communication and support. We once had a director who seemed to be struggling with every deadline. Instead of moving straight to transition, we discovered through these questions that they needed more regular check-ins and clearer priorities. After making those changes, they became one of our strongest leaders.
But when it's not enough, you need to get honest about what the organization needs. When we spend countless days, weeks and months trying to make it work with certain folks, the only thing that's always true is that frustration grows all around. The reality is, once you know, you know. Delaying acting on that knowledge isn't fair to anyone - not the person in the wrong role, not their teammates, and not the mission we're all there to serve.
-
Instead of making decisions FOR people, I give them the opportunity to opt in or out of the role. This might sound unrealistic - who can just give up their salary and benefits? – but how you approach it is what matters.
First, you're crystal clear that things aren't working as they are. Then you have an honest conversation about whether they want to be here. If they do, there need to be specific, immediate changes with very little wiggle room. If they don't, you offer direct support to get to their next step, including a generous severance package.
This approach works because it:
Prioritizes agency - people get to make real choices about their future
Maintains relationships - avoiding the trauma of surprise terminations
Creates clear paths forward - both staying and leaving are dignified options
Allows for genuine choice - severance makes it a real decision, not just financial pressure
If someone chooses to stay, they're truly committed. They know exactly what's expected and they're ready to work for it. But most of the time, in my experience, folks choose to move on - doing so with their head held high and with support for their next step. Both are successful outcomes!
I once had a team member who was struggling with our fast-paced environment. Instead of just letting them go, we had an Opt-in Conversation. They admitted they were exhausted trying to keep up and actually wanted to return to a more structured role. We were able to provide transition support, maintain a good relationship, and eventually even became a reference for their next position.
The Business Case for Generous Severance
Let's be honest about our financial reality - we're all living and working in a capitalist society where our lives often rely on us being employed. I'm a BIG believer in generous severance, especially as part of an Opt-in Conversation.
Why severance works:
Gives people runway and reduces stress so they can make an honest choice
Communicates respect and recognizes the real human impact of transitions
Honors their contributions and acknowledges that everyone was part of things not working
Builds team trust by demonstrating you value people even during transitions
Yes, this is an investment and your budget likely feels tight. But I'd argue that keeping someone in the wrong role costs more - in team morale, lost productivity, and missed opportunities.
What we generally do is drag our feet - throwing money and time at trying to solve something for months before having an Opt-in Conversation. This isn't serving anyone involved. How much more beautiful and straightforward to have the conversation earlier and then focus on the work!
Secret Sauce & Takeaways
Trust your gut: When you know, you know. Delaying action isn't fair to anyone
Mission over comfort: Your organization's purpose should guide these decisions, not your fear of difficult conversations
Give real choices: Severance packages enable genuine decision-making rather than financial coercion
Clean is better: Quick, clear transitions serve everyone better than drawn-out attempts to fix fundamental misalignment
Generous severance pays for itself: The cost of keeping someone in the wrong role almost always exceeds severance costs
Questions to Ask Yourself
What is my company/organization’s primary purpose, and how should that guide transition decisions?
Am I spending disproportionate time trying to make one person work instead of focusing on the broader team/our work/mission?
Have I been crystal clear about expectations and support needed?
What would treating this person like I'd want to be treated look like?
Am I avoiding this conversation because of my discomfort or because it's actually not the right decision?
Want to Try This?
Templates & Guides:
Our Opt-in Conversation Guide with step-by-step scripts you can adapt and email templates for communicating transitions to teams and clients
Recommended Reads:
Netflix Culture Deck - this is some of our foundational thinking on performance and transitions - has shaped + informed how Jess @Helia approaches almost all things people for decades now!
Radical Candor - excellent resource on having difficult conversations with care (and for a quick intro, Kim Scott'sTED Talk on Radical Candor is one or Jess’ personal favorite introduction to these concepts
Connections:
Helia Collective members Nina Jacinto and Sophia Zisook are both beautifully experienced in org restructures and layoffs and thinking about all the ways that you are making decisions for both the human and the organization. Wonderful thought partners to help think through individual moments AND the bigger picture of how you’re approaching this.
Remember: Always get appropriate legal and HR review before having these conversations. This approach has worked for me, but every situation and organization is different.
As always, take what's helpful, leave what's not, and make it your own.
