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4 reasons why you definitely shouldn't hire a Chief of Staff
There are probably more, but these are the big ones to watch out for
Everyone’s got something to sell, including me, but bad advice doesn’t help anyone.
In recruiting, bad advice or guidance is ruinous. Everyone loses:
Clients are ticked off because the recruiter oversold themselves
Candidates are upset because the recruiter oversold the company
The recruiter’s reputation and business suffers as a result of both
While this might not be that big a deal if an agency is making thousands upon thousands of placements a year for more junior roles — after all, the next placement opportunity is right around the corner — it is a HUGE deal if you’re a specialized recruiter in a very specific niche like Chief of Staff placements.
On face value, and regardless of the role, a recruiter is incentivized to sell you on their services and candidate pipeline. Landing you as a client + placing a candidate = $$$. Pretty straightforward.
At no time does a recruiter try to convince you why you don’t need to bring someone new on your team, but that’s exactly what I’m going to do now for the Chief of Staff role. Here’s why you should second-guess hiring a CoS:
1. You actually need another executive
This can be assessed a couple of different ways.
As the CEO, take a look at what you’re spending most of your time on. Is 75% of your day spent on biz dev/partnerships? Are things falling through the cracks because you just can’t keep up with your inbound? Founders are hardcore evangelists and the consummate salespeople, but most of them absolutely abhor the minutiae of follow-ups and the list of tasks that must be executed to go from intro call to closed deal as fast as humanly possible.
I know what you’re thinking: a Chief of Staff with partnerships experience is exactly who I need. But maybe not.
Who else on your team is working on partnerships? Is product or customer success involved? To what degree? Are there other salespeople on your team that need a dedicated leader to manage and coach them? Another way of looking at this: where are the obvious gaps in your org chart today and how do you expect your org to evolve over the next 6-12 months based on your key strategic objectives?
Remember that a Chief of Staff isn’t just brought in to do one thing — they can draft business plans, create processes, implement systems, stand up departments, gap-fill on high-priority projects with no owner, etc. They’re expected to do a lot of different things and do them well, whereas an executive is laser-focused on their function and team. There are many situations where bringing on an executive instead of a Chief of Staff makes a lot more sense. Which leads me to my next reason to re-consider hiring a CoS.
2. You’re not scaling headcount
If you just closed a round and have a boatload of cash to spend on expanding your team like a maniac, then kudos! That’s no small feat, especially in today’s fundraising environment.
But when the chips are down, or you’re in the fortunate situation where you can do more with less and scaling headcount isn’t critical to your growth strategy, it might not be the best time to bring on a Chief of Staff.
One of the huge advantages of a CoS is that they help their Principal (the person they report to) and the executive team become more efficient. Their presence on the team becomes a more obvious need when 1) you’re expanding the executive team, and/or 2) you’re growing the rest of the org at such a fast clip that processes and systems are becoming more critical. Here are some examples of this:
Your exec team is growing. You’ve got a handful of VPs or C-suite execs on payroll now, quarterly planning is coming up, and your first annual planning session is looming. It needs to go off without a hitch because your board meeting is around the corner and investors will want to see what your plan is for the upcoming year. Who is going to run these meetings? How will they be run? What tools or templates will you use during planning to ensure you’re discussing the right thing? What’s the plan to communicate your objectives with the rest of the company? The Chief of Staff is usually your go-to here. If your exec team is just 1 or 2 people, you’re probably better off sticking to the more informal meeting structures that have served you well up until this point.
Processes and systems are…non-existent. Or they’re just bad. Startups in particular can “get away with” growing really fast in the absence of formal processes (e.g. interview and onboarding processes) or even entire departments (see: HR…yikes!). I’m talking orgs with 100+ people — very painful for employees! Especially if you’re a highly matrixed company where efficiency gains due to a process improvement in one functional area can compound across the org. At a certain headcount number, employees start demanding at least some standardization of processes and new systems, or things like communication, job satisfaction, and morale just start to break down (and it’s hard to recover from some of the damage done to the company culture).
The tough thing is that there is no natural owner of “processes and systems”. If no one owns it and they’re not getting goaled on it, nothing is getting done. If you find you’re lacking in these areas and your teams are crying out for some law and order, then you’re probably in need of a Chief of Staff. They are the ones who will lead the audits, identify your most critical problems, come up with a few solutions, and execute the plan to a T.
3. You just need an EA
After auditing your needs as a CEO, ask yourself if you really need a Chief of Staff, or if you just need an executive assistant. An EA can unlock a ton of value for you (like more time) via gatekeeping and taking pesky tasks like scheduling and travel logistics off your plate.
I know a ton of founders who also have their EA work on personal or household admin stuff like planning trips, researching schools for their kids, booking dinner reservations, and more. The rationale is that they free up their time so they can spend more of it on their business. Makes sense!
One question to ask yourself is: how much time do I need this person to spend on strategic initiatives that move the needle for our business vs. administrative work? The fact is, they should spend 95% or more of their time on strategic initiatives, with the remaining 5% being the natural admin tasks that arise from their own endeavors.
Here are some mistakes that are made with respect to this:
The job description isn’t explicit. There might be a decent chunk of admin work that’s expected, but it’s not included in the job description for whatever reason. Solid employers know what candidate they need and want to attract, so good Chief of Staff job descriptions will say things like “this is not an administrative role” or “this role is equivalent to a Senior Director”.
The candidate doesn’t get clear on expectations. The interview process is as much as an evaluation of the candidate as it is of the employer. It’s absolutely imperative that candidates seeking a Real Chief of Staff™ role screen out employers who don’t meet their benchmarks when it comes to how much time they’ll spend on strategic initiatives. Make sure you ask what percentage of your time will be spent on administrative tasks. If you’re worried about how you might come across — e.g. someone who’s not a team player, someone who doesn’t want to do work that’s “beneath them”, someone who has a big ego, etc. — don’t be. You can always mention that based on your background and experience, you add the most value when you’re focused on X, Y, and Z, not administrative work.
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4. You don’t see a reasonable career path for your Chief of Staff at your company
The ambiguity surrounding the Chief of Staff’s exact responsibilities is a double-edged sword for both the candidate and employer.
From the candidate’s perspective, you get to explore and move the needle for different functions within the org. If you’re not sure whether operations or biz dev is more attractive as a next step in your career, the ambiguity of the Chief of Staff role is a boon. From the employer’s perspective, they can keep the job description vague enough to intrigue the right candidate but broad enough to retain the flexibility to deploy them across various initiatives as needs arise without letting someone’s expectations down.
Where it starts to get dicey for the Chief of Staff is when role ambiguity translates to a lack of KPIs. The Chief of Staff role is possibly the only role in the entire company that doesn’t have responsibilities with explicit objectives and key results that ladder neatly to company objectives. So, yes, your Chief of Staff gets a lot of stuff done, but without OKRs, there’s a risk that you begin to see them as a task completer. This pigeon-holes them into the role and can hamper their ability to move beyond and above it.
While it’s natural that the Chief of Staff’s responsibilities evolve over time, I wouldn’t advise hiring them if their transition out of the role is a complete black box. The general career path for a Chief of Staff is 1 of 4 things after about 12-36 months in the role:
Transition into a leadership role within the company
Do the same as above, but at a different company
Start their own company
Stay in the role for life (quite rare as CoS tend to be highly entrepreneurial individuals)
Understanding your leadership needs over the next 12-24 months and uncovering your Chief of Staff candidate’s goals and aspirations through the interview process will help you align more closely with the right person for your team.
Still think you need a Chief of Staff?
If you’re a CEO hiring a Chief of Staff and found this helpful, want to do a deeper dive on any of the above, or need help accelerating your Chief of Staff search, I’d love to talk. Just shoot me a DM on LinkedIn!
If you’re a candidate looking to get placed as a Chief of Staff with Right Hand, be sure to submit this Typeform!
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Until next time, Right Hand fam! 👋