Four Ways to Leave a Leadership Job You Love
The necessary moves to feel good about your next necessary move
This Friday marks my last day as the Director of CX at Calendly. I’ve been at this company just shy of 3 years and boy, has it been a ride. I could write a very thrilling “25 minute read” on what I’ve learned from working, growing and experiencing things here. But this 8-minute read is different. In the few weeks since the announcement of my resignation, I’ve been focusing on making this transition smooth. It’s important to understand that it was an incredibly difficult decision to leave Calendly, as I am deeply attached to the work we do. Today, I am ready for my big change (which you can read more about at the end) and these four steps helped me get there.
1. Feel good about your legacy.
This is a personal and emotional step. This is a ‘get inside your brain and understand this’ step. Think about how you would define the impact you personally had on foundational pillars like processes and people.
It’s important to take an objective account of the work you’ve accomplished and understand what processes you’ve created that will ensure a foundation for further success. Take a good look at the growth your team and company have seen because of research and decisions you’ve been a part of. Take a look at the impact your team has had on the company. Where did your biggest project land and what did it do?
For us it was getting our First Response Time down to 15 minutes across all user segments (!!). This seemed impossible, but not one support person bat an eye when I presented this challenge. We came up with extended shifts, re-focused workflows, and presented the plan with vigor and excitement that permeated throughout the team. Everyone knew we were in it together and felt excited and compelled to get it done. It took us less than 2 months to get it right: fast response time with no degradation in experience. We average <15 min blended for all user segments, and our commitment to this goal is the core of how we operate.
Now think about the people. Think about the new hires you have helped grow into superstars. Think about the motivated, hungry, self-starters who turned into your best managers. Think about the direct reports who worked with you tirelessly to improve and how far they have come. As I prepare to leave, I’m thinking of my team as we worked together through the hardest days, the people who have become my greatest friends, and mentees that I’ll continue to work with long after this role ends.
Know that these things exist and they are concrete. You did that and you were the catalyst for growth and evolution of your team. You quadrupled it in size, and you created the culture where genuinely, every single person loves coming to work and focuses on doing right by others.
Don’t deny yourself this internal review of your work. After doing it, I am very confident in the future of this team because of its incredible people and our tried and true processes.
2. Prepare your successors.
Officially or not, there are people who your responsibilities will fall upon. Don’t leave them hanging. If you’re like me, you’ll feel better and less guilty if you over-communicate, giving them every sliver of information they will need to be successful. For this part, I created a playbook, a roster run-down, and a daily-double check.
Maybe you’re that rockstar employee who has been working on a “how to do this job” since your first day, but for most of us, we’ll complete our playbook in the weeks leading up to departure. Since my team knows the day-to-day processes well, mine focuses on all things CX Leadership at Calendly. There’s a list of our tech stack, who our contacts are and where we’re at with renewal. There’s a breakdown of how to pitch new softwares or big ideas, and nuanced details like adding triggers to Zendesk and recommendations on what to approach next. There’s an entire section dedicated to cross-departmental function and how my role interacted with each one to make sure those lines of communication are kept open. There is leadership advice, the inevitable “how to do the expense report,” and a reminder to always keep CX core values in mind. It’s long and exhaustive, but I know if someone has questions, they will have the resources they need to find the answers. Do this for your successors, but also for you (surprise!) It’s a quick glance of the work you have been responsible for, and reminds you of your impact. Be proud of that.
Next, the roster-run-down. If you are a people-leader first, manager-later type of gal like me, you may feel that your most important job before you leave is to make sure each of your team members is set up for success, and part of that includes them having the same passionate advocate in a new leader as they had in you. I had the luxury of sitting down with our new Head of CX and spent a whole hour going through each of our support humans. I detailed their hopes and dreams, what they’re great at and where they can improve. I shared their journey, their intricacies and where I think they would be most successful. I shared what excites them, what makes them tick, who is new and who’s ready for their next move. His response was warm and grateful to have this insight to make the transition seamless and keep morale high.
The daily-double-check is just an attempt to be hyper-aware of what is falling on your plate each day and make sure it’s either being formally delegated or written down. As a leader, especially in support, there are endless small but mighty tasks that appear. Often they are quick no-brainers that leaders don’t tend to think about. Think about this though — if the answer lives only in your brain, your team will be in big trouble the next time that one-off task comes around and your brain is in a different office, communicating in a different Slack group.
3. Tie up loose ends.
Don’t leave unfinished business that is less than one or two steps away from being completed to your successors. Finish any projects you have pending, confirm decisions that are still “in the air,” and put anything currently on hold back in action if you feel it’s important enough. Get those looming questions answered and cross every item off your checklist if you can control it (hey, Dopamine!). And it’s not just about you: Get your team members those promotions they so deserve, close out pending deals, and answer the emails that have been sitting for months (ok, this does not apply to me, I am always inbox zero, baby!)
If tasks are inevitably left unfinished, make sure your successor has the work you’ve completed (research, recommendations, and emails sent) so they can make an informed decision. Provide facts, details, and a write-up on how you’ve come to the conclusion thus far and the next steps (see Playbook above!). Set your team up for success, they have enough to do!
4. Get pumped up for the new gig!
Next week, I’ll be starting as a Senior Manager of Support at Samsara. They have a 1-year old Atlanta office with a budding support troop and I’ll be joining the management team to help them grow and scale at a very fast and exciting pace — which reminds me of a place I started at a few years ago 😉. I still don’t quite have the elevator pitch down, but I understand the basics of what Samsara provides to its customers. I know their offering is exciting from an industry perspective, but for a while I was simply taking the word of the people who interviewed me. They have to say that Samsara is changing the way organizations do business — which is why I dove into product research.
Before day one, I spent multiple hours learning about the product suite, hardware, software and services, and I got excited. Ex: Schools use Samsara to safely and effectively transport kids to and from their homes, real time tracking, dashboard cams — a parent’s dream! I geeked out over the importance of improving fleet technology and I’m excited to learn more. Once I do that, I can get my hands dirty and implement support techniques to get Samsara customers the answers they need efficiently.
I believe in Calendly’s product with all my heart, and it played a huge role in committing to this job everyday. I was terrified to never find that again. Through some pre-work before diving into product training, I now am certain that I’ll feel the same way about Samsara soon. So do the pre-work. Get into the nitty gritty and nerd out, because it’s a lot easier to say goodbye when you’re invested in the adventure ahead.
BONUS: Make your first day the all-company SKO.
My first day at Samsara is also the first day of their 2020 Sales Kick Off, where the entire company from all three offices will be in SF learning about the big, mind-bending company plans for this year and beyond. I’ve never been to a SKO at Samsara, but I’m guessing there’s a lot of hype, a lot of excitement and a lot of swag (which I love so much). If I have any doubts or worry about my decision, I know for sure they will be quickly squashed by what will very likely be a huge room of like-minded excited and ambitious people ready to take the world by storm, and that’s all I’ll need.
All wrapped up: If you commit to something the way I do, especially your job, it’s really hard to leave. I’ve done it once before and it nearly destroyed me. But change is important, growth is imperative, and challenging yourself away from comfortable is the only way to stay alive (metaphorically speaking). So get super self-aware and go through the motions necessary to make the jump as seamless and feel-good as possible, because if you don’t getting a running start, you may not stick the landing.
Calendly, thank you for every single moment. As my first CEO at Yext, Howard Lerman always says: “Onward!”
