We’ve written before about how to be a senior leader. But at very senior levels, when you actually run a complete department, there are additional factors that you need to consider in order to be successful.
When we talk about the head of a department, we’re referring to something like this list from Snowflake, excluding the CEO and Cofounders. This list comprises the senior leaders of their functions: all have unique roles, and most are direct reports to a CEO or C-suite executive who runs multiple disparate functions (the most common title for this non-CEO executive is President).
The litmus test of whether you’re in this group: you are and/or report to a C-level executive, and your role is unique within the company.
All of the advice in this post stems from 4 factors:
- Your boss can’t be your coach
- You’ll be unique among your peers
- You’ll own your department’s budget and structure (and as a result, will be the arbiter of rewards and who is a part of the team)
- You will be the external face of your organization
Let’s dig into how these factors impact the job, and how to navigate them.
Grow Without Coaching
The first rule of running a department is that department leaders don’t get much real coaching. You’re hired (or promoted) to be the expert in your function – if your manager has experience in your field it’s likely a coincidence, and if they’re a long-time CEO your experience is probably more up-to-date. CEOs are usually very smart and are often invaluable for general management or strategy advice, but when it comes to the details of your field you’re probably the one who’s most up to date.
Since your manager won’t be an expert in your field, succeeding will be both more difficult and judged more aggressively.
Employees are usually evaluated on skills (can you do X), observed behaviors (did skill X let you take Y action), and outputs (did Y action lead to Z). If your manager can’t coach you, however, they won’t have a strong opinion on whether your skills or behaviors were correct until their output can be observed.
As a result, assessment of your performance will be:
- Almost entirely based on outputs, with less nuance about (e.g.) how easy or hard your job was, or how reasonable your goals were
- More sudden, since assessment will be less frequent
- Less helpful, since it will focus primarily on outputs
Your manager will also know that working with you to improve (significant) issues is likely to be very time consuming for them in the best case, if it even works at all. If your department’s outputs are unacceptable, the standard solution will not be to train you, but to replace you – even if you are just unlucky.
The best way to handle this situation is to avoid it entirely by thriving. One additional wrinkle, however – if the company is growing fast, high performance isn’t a static target. In times of high growth next year’s expectations can be significantly higher or different than today’s.
A few steps to take:
First, you need to set your CEO’s expectations. This requires active education, particularly if they aren’t experts in your field. You’re trying to get on the same page with them regarding:
- How to measure success, ideally pre-aligning on outcomes
- What steps you’re going to take (this often requires the most education)
- Why these actions are important, and what they should expect if they go well/poorly. In addition to building alignment, reliably calling your shots is the best way to build credibility
Then find mentors who are 1-3 years ahead of your company’s stage. You’ll get a bunch of different answers, so use these conversations to establish a map of where your machine needs to be 12-18 months out. Creating this map allows you to minimize disruption on the scaling road – for a small but critical example, it will be much easier to gradually evolve your org chart towards the structure you’ll need in the future, rather than overturning everything with a massive reorg later.
Next, find an executive coach who’s familiar with your field. Many executive coaches are bullshit artists, but some are not. Interview several via complimentary intro calls. Get exec coach referrals from the peers from bullet point #1, your network, your manager, or your investors. More people than you might think have executive coaches, and it will not reflect poorly on you to ask around for recommendations.
Round this out with feedback from your executive peers (you should already be getting feedback from your team) – ask them how they worked with your function at other companies, what went well and what didn’t, and then process it all with a healthy grain of salt. You should also use any feedback sessions to help educate them on what your function does (they’ll be even less expert than your manager), and educate yourself on what they do (they’re in the same boat as you).
Scale the Undelegatable
As you scale, the total amount of things that only you can do increases to the point that it can literally exceed the number of hours you have in a week.
There are two categories of tasks that you cannot delegate: External tasks where counterparties will be offended if you don’t send an appropriately senior leader, and internal tasks that require the neutrality and discretion of someone who oversees an entire function.
External jobs to be done include:
- Representing your function: speaking at your company events or conferences, to investors, or to the press
- Dealing with high magnitude external escalations: very upset customers or partners, lawsuits, or service provider issues
- High stakes sales: closing your biggest customer, getting acquired, raising venture capital or going public
Internal jobs to be done include:
- Anything that requires privileged knowledge of compensation and hiring plans: approving and advocating for budgets, creating new teams
- People management in sensitive situations: Approving promotions, hiring of new leaders, and terminations
- Reconfiguring team dynamics: Performance managing senior leaders, arbitrating conflicts between teams, reorgs
Worth calling out in case it wasn’t incredibly obvious: many undelegatable activities are escalations. In addition to being stressful, that means that the tasks you can’t farm out are also impossible to schedule. There is no amount of planning that will prevent a major HR issue from arising the same week that you’re getting acquired and closing your largest customer.
The normal advice on scaling is to find great people you can delegate to, but by their nature these tasks are difficult or impossible to distribute. You can’t just say “talk to Alice about bonus amounts if you can’t find me.” Instead, you need to find people who can help shoulder the load piecemeal.
The best solution I’ve seen is a single partner who can be the internal or external delegate for your function. One classic example is the trusted VP of Engineering / Product who has full command and control over the team, and a CTO / CPO who talks to investors and customers in between kissing babies for the cameras.
This solution is nice because each of you can also theoretically take a real vacation. The difficulty is that it requires finding a yin/yang pairing in which one person prefers being external-facing and the other prefers the opposite.
You can also establish lieutenants who can operate with minimal guidance internally and help shoulder a few external tasks – perhaps one can handle partnerships, or another is great at sales. You may not be able to delegate to them fully, but by virtue of their versatility they can provide more buffer for your organization. This structure is more complex to manage, but great for succession planning as it builds a diverse skillset across your department.
Building out an operations function is another strategy that can complement either of the above by minimizing the burden of internal tasks. Operations teams are double-edged sword, however – in the best case they’re a godsend, in the worst case they create more work than they remove.
Disagree and Fully Commit
When you’re the head of a department you have an expanded role in the culture of your company. In some ways your job as a department head is similar to being an Individual Contributor, where your “team” is the executive staff. What that means – you need to disagree and fully commit. No grumbling, no eye-rolling, no passive aggression.
This is a subtle shift. There are definitely leaders in organizations who hide behind the idea that they don’t agree with the company’s strategy, but are going along with it just because. I think of this as Disagreeing and Sorta Committing, and it sounds like:
- “This is the plan, but I don’t think it’s going to work”
- “Well, this is what the higher-ups said”
When you’re a department head you are “the higher-ups,” and visible fractures in the executive team erode confidence in leadership. If you publicly say Left when the company strategy says Right, you can cause chaos immediately. As a department head you have to fully commit, maybe not with a smile on your face, but with the understanding that the odds are usually better when everyone follows a singular strategy.
Build and Wield Your Credibility
Of course, Disagreeing and Fully Committing doesn’t mean that you don’t speak up. Heading a department means that you have access to the CEO and deep expertise – you have a duty to turn that expertise into credibility by having high-quality strategic contributions, and wield it to help the company succeed.
I’ve heard executives say versions of “I would raise
To run a department effectively, make sure that you:
- Learn how to grow without coaching
- Scale your undelegatable tasks
- Disagree and fully commit
- Build and wield Your credibility
For one final thought: running a department is akin to being the CEO or GM of a mini-company that produces your function’s special sauce – whether that’s a sales quota, working code, or a pipeline number. As a result, a lot of the advice and literature that applies to being a CEO also applies to running a department, particularly at scale.
– The SaaSy PM, with heavy input from the SaaSy Engineer