Let’s imagine you start working at a fast growing organization called Dragon, Co, just before the peak of its heyday. The whole company, at this point, is around 50 people. Everybody knows each other’s names. Together, you built and iterated on the first public launch of a brand new thing. And, great news for you: The world ate it up. Sales have been so good that there was even more demand than expected, and it becomes clear that you’re going to need to scale faster — and better — than ever before.
To gear up for v2 of your great thing, you all dive deep into planning and recalibration mode. Department heads rally their teams and talk about little tweaks to iterate on for the next launch. You start making a few hard choices about the product itself. You change your marketing strategy. You add a few new people to the team. Things are changing a bit faster than you’d expected, but you try not to overthink it. We’re moving crazy fast, you tell yourself. But at least we’re all together. We can do this.
And then, a shoe drops. In an all-hands meeting, some new person — let’s call her Susie — is introduced to the company for the first time. Susie, so they say, is the secret sauce needed to get Dragon, Co from A to B. She’s been there before. She’s seen this stuff in previous jobs. That’s exactly the kind of thing we need right now, they tell you. We know you’ll all love her.
This sort of thing has never happened before, so naturally, you and the team need a minute to process. But then, one person — let’s call him Derek — one of those all-star individual contributors, and also the kind of guy who’s always had a surprisingly effortless relationship with the leadership team, pipes in without skipping a beat to ask:
“But what about Trish?”
The room gets a little quiet. That’s right, you suddenly consider. What about Trish? As one of those super early hires, Trish was the one who started a team from nothing, eventually leveling up to become not only an effective internal leader but a cultural champion as well. She’s the kind of person who always puts a smile on your face, who has a knack for remembering even the most personal (albeit benign) details of everyone’s lives. But it sure seems like Trish’s job and Susie’s new job have a lot in common, which doesn’t seem to make a lot of sense. The place wouldn’t be the same without her around. But you only need one person to do the job. So is it Trish? Or Susie?
The response only adds to your discomfort: “Let’s talk about that later. And now, moving on…”
By that point, of course, everyone’s heads are spinning. If Trish is out, you might start to wonder, who else is next? What about the rest of her team? What about Mike? And…what about me? Could I be next?
How you say goodbye
Transitions are impossibly hard. Senior level role transitions, even more so. But they happen all the time.
In an annual survey that we sent to employees across USV portfolio companies last year, we found that 80% of companies in our network had experienced some transition in leadership at the executive level in the previous calendar year. That’s right: 8 in 10 startups went through some sort of leadership change in one year.
On the one hand, this might seem like a lot of transition for fast-growing organizations, something that might only add to feelings of instability or uncertainty. On the other hand, the idea of “scaling up” to find new people who are custom-fitted for a later stage of a company’s growth makes a lot of sense. Of course, this doesn’t make transitions any easier. Particularly when the person in question was beloved by the rest of the company.
So this begs the question: As a leader, how do you say goodbye to employees who are on their way out of the organization?
To me, this feels like one of the most pivotal moments to establish one’s stance as a leader. And it likely leaves you with a lot of questions to answer: How do you introduce the new person? How do you thank the outgoing person? Do you celebrate their wins publicly and thank them for their service? Or do you slowly phase them out, avoiding any unnecessary attention?
Whatever behavior you model is magnified and multiplied by the rest of the organization. All eyes are on you. And every interaction will be captured and catalogued by the rest of the group.
It doesn’t matter whether this type of announcement happens in person (like the hypothetical all-hands meeting with Susie and Trish), via email, or in a smaller meeting of department heads. From that point on, everyone else will be laser focused on how you refer to the departing employee — from the way you refer to them when new people ask a question to the way you acknowledge or dismiss the work they did in a casual Slack chat.
In times of change management or transition like this, every moment matters. As a leader making the call, it just might come to define how you’re perceived by others for a very long time to come.