Nine steps to set your deputy up for success

For many leaders, there comes a time when you can’t be with your team for an extended period.

Say you’re going on parental leave or sabbatical. Since you’re invested in your people, I know that one question will begin to nag you from the moment you consider a leave of absence: who is going to lead your team while you’re away? Who is going to guide, support, and challenge the team as a whole and each individual on it?

Of course, you could just ask a trusted peer to take on your team and you’d know they’d be in good hands. But by doing so you’d miss an incredibly effective and rare opportunity to grow the next generation of leaders in your organization: entrusting a colleague from a lower career level to serve as your deputy.

Your deputy will not only acquire new leadership skills and hone their existing ones; they’ll also get access to people and information that were previously out of reach for them, which will likely unlock even more opportunities for them down the road. And they’ll have a sneak peek into what it’s really like to work in your role, helping them to determine whether they ultimately want to pursue the same career.

A year or so ago, I deputized for my former manager at Babbel, in the role of engineering director. Some months later, I appointed one of my direct reports to serve as my own deputy, i.e., as an engineering manager. Having experienced deputation from both perspectives, here I’m sharing my advice on how to set your deputy up for success.

I recommend documenting the nine steps suggested below so that your deputy has an artifact to refer back to while you‘re on leave!

1. Identify the North Star

You can’t possibly predict every task your deputy will have to do nor every challenge they will have to overcome during your absence. What you can do, though, is provide them with guidance that will inform their decisions along the way. Give them their North Star to follow!

Consider this direction, which I set for my deputy:

Enable the team to deliver well-engineered product increments, which address our users‘ needs and are aligned with our area‘s objectives, through continuous experimentation.

There’s quite a bit to unpack here… It’s important to dissect and discuss your North Star statement together with your deputy-to-be, so that they can internalize it. It can be helpful to play out some imaginary situations they might encounter. Together, identify the trade-offs that arise and discuss how the North Star points them in one direction or the other.

The North Star will give your deputy assurance: as long as their actions contribute towards following the star, they know they’re on the right path.

2. Establish the ‘make-sures’

Even if you could, you wouldn’t want to leave overly prescriptive instructions on how your job is to be done. After all, your aim is to empower your deputy to really fuel their professional growth. Having said that, they will need a little more than just a North Star statement to fully understand their new responsibilities.

List the three to five key responsibilities you want your deputy to dedicate most of their energy towards. Explain not just what the responsibilities entail but also why you deem them important. For example, I listed ‘Conducting 1:1s with all direct reports’ as one key responsibility and went on to explain that 1:1s allow me to keep my finger on the team’s pulse, exchange feedback, build and maintain trust, do sense-making, and so on.

This is also a good moment to explicitly set expectations. What performance can you reasonably expect from your deputy considering their current skill set, their prior experience, the duration of your leave, etc? It’s likely that they’ll feel intimidated by their new responsibilities; they might even struggle with imposter syndrome. By clearly setting and communicating reasonable expectations up-front, you can help to reduce any potential anxiety.

3. Define what’s out of scope

Almost as important as defining the ‘make-sures’ is establishing where your deputy’s responsibilities end.

Do you have isolated responsibilities that you could split off and assign to someone else? For example, in addition to leading one product team, I was managing the 24/7 on-call roster of the entire product area. In an effort not to overwhelm my deputy, I delegated this responsibility to a different colleague (for them, too, this represented a potential growth opportunity).

There could also be legal limitations that prevent you from delegating some of your responsibilities to your deputy. For example, they might not receive the power to implement salary raises or to sign contracts with vendors. You’ll have to find someone else (e.g., your own manager) to ensure these responsibilities are covered in your absence.

4. Confirm any deliverables

In our line of work – people management – we deal with fewer tangible deliverables compared to the work of individual contributors. Still, they do have their time and place. Think about whether your deputy is supposed to deliver anything in particular to a third party or to you upon your return: a presentation at a department or company all-hands, a development plan for an under-performer on the team, a pitch to the execs…

When I returned from my three-month leave, the bi-annual, company-wide performance reviews and development talks were scheduled to occur. I missed half of the evaluation period, so I was relying on my deputy to assess each direct report during my absence. Unfortunately, I’d failed to explicitly request these assessments before I left, which would have spared us both some busy days immediately after my return.

5. Provide a support network

North Star, make-sures, deliverables – that’s a tall order for someone new to the role! It’s inevitable that your deputy will face a challenge they feel they can’t solve alone.

This is why it’s so important to provide them with a support network they can tap into. Identify a set of complementary colleagues that can support your deputy in performing the different responsibilities. Ask these colleagues if they‘re motivated and have the capacity to provide support to your deputy, even ad-hoc if need be.

For my deputy, my own manager and the product manager of our team were obvious choices. I also briefed the HR business partner, who was assigned to our product area. Most importantly, I enlisted a fellow engineering manager to serve as my deputy‘s mentor. I suggested two candidates to my deputy: a seasoned EM and an EM who went through the transition from the individual contributor track to the people management track in the not-so-distant past. My deputy chose the latter, as they felt they could relate better to their situation. (And you guessed right: the candidate hadn’t mentored aspiring managers before, so this represented a potential growth opportunity for them, too!)

In the weeks leading up to your departure, initiate some informal get-to-know-each-other chats between your deputy-to-be and each member of the support network they don’t or hardly know. This will reduce the mental barrier for them to actually reach out for help when needed while you’re gone.

6. Consider critical skills training

This section requires the most customization to the particular colleague you have chosen to become your deputy. Although you’ve chosen them because of their strengths and potential, I can assume there’s still a gap between their current skill set and the skills required to perform in your role. Depending on your timeline, it’s probably unrealistic to expect to close this gap entirely. Nevertheless, it’s worth it to invest in decreasing it as much as possible.

Together with your deputy-to-be, reflect on the key responsibilities you’ve outlined above and the skills they need to acquire or strengthen to meet these. Then, work out how you can train your deputy in those skills.

In addition to mentoring the deputy myself, I also signed them up for LeadDev Together, a course that taught fundamental engineering leadership skills and was conveniently scheduled shortly before my leave of absence started.

7. Prepare for meetings

A good part of a manager’s week is determined by meetings, which come in all shapes and forms. Their nature can range from tactical to strategic; the manager’s role can be owner, facilitator, or participant; the list of attendees can be very short or quite long; the group of participants may be homogeneous or diverse; the meeting’s duration may span minutes or hours; and so on. It’s not hard to imagine that your deputy might feel lost when they start to receive invites to the meetings they’re to attend on your behalf.

That’s why I suggest giving them an overview of each of your recurring meetings in advance. For each meeting, provide the following details: title of the meeting, its purpose, its owner, your role, and the importance you assign to it.

Compiling this information not only provided my deputy with a helpful overview, it actually turned out to be a fruitful exercise for myself, too, as it required me to take a step back from the day-to-day busyness. Explicitly articulating the purpose for every meeting revealed opportunities to sharpen our focus for some of them, making them more effective. And by assessing the importance of each meeting, I realized that in one instance I could alternate attendance with our product manager, which resulted in a more efficient use of our time.

I suggest inviting your deputy-to-be to all these meetings in the weeks leading up to your departure. As your shadow or potentially even as an active participant, they can start to familiarize themself with the respective meeting and its attendees.

One more note on meetings: if your deputy-to-be has been working as an individual contributor, I recommend discussing with them the difference between two types of schedules, which Paul Graham dubbed the maker’s schedule and the manager’s schedule. I expect that the fragmentation of the manager’s schedule will initially pose a challenge to them, as it becomes much harder to work in an uninterrupted fashion. You can help them by teaching them strategies to allocate focus time despite the transition.

8. Take care of the logistics

Before your deputy can take over for you, there are likely some logistics to be taken care of. The challenge here lies not so much in implementing them but rather in identifying all that needs to be done. For example, you don’t want your deputy to miss out on critical information only because they weren’t added to a relevant mailing list.

Here are some things you may need to consider:

• Adding your deputy-to-be to calendar invites, mailing lists, and chat groups 
• Providing them with access to relevant tools or information
• Configuring them as an escalation layer in on-call schedules
• Signing them up for critical notifications, e.g., budget alerts of your infrastructure 
• Granting them privileges to perform certain tasks, e.g., approving vacation requests or invoices

9. Hand over the reins

When you’re about to start your leave of absence, consciously hand over the reins completely. Please, resist the urge to check in with your deputy occasionally. The time has come for them to lead and to make their own mistakes. You’ve equipped them with the knowledge and skills as well as a strong support network to perform your role successfully. You can trust that, no matter what, they’ll do their best given what they’ll know at the time. They’ll be fine. Your team will be fine. Enjoy your leave. When you eventually return, you’ll find that your colleague will have grown professionally significantly.