It seems that a lot of startup firms are hiring these days. Or at least thinking about it. So, I thought I would use this column to talk about hiring – especially hiring those first “real” employees. By that I mean the first hires that aren’t just extra hands doing the same thing the founder already does, but people meant to take on a whole piece of the business the founder has been carrying alone.
The thing I notice is that, almost without exception, when I ask to see the job description they are about to post, it describes a title, not a job.
If they need help with sales, they write a job description for a sales manager. If they need help with marketing, they write one for a marketing manager. And what goes into that description isn’t really a description of what their company, at this specific moment, needs someone to do.
Instead, it’s a description of what a sales manager or a marketing manager is generally understood to be — pulled, consciously or not, from a job board template, or from whatever the founder’s last employer called the role, or from whatever LinkedIn seems to think the title requires.
In other words, and for whatever reason, it is usually a generic job description describing a generic job.
This matters more than it might seem at first glance, because of what happens downstream. A generic title attracts generic applicants — people who read “Sales Manager” and picture the Sales Manager job they’ve had before, which may look nothing like what is needed. You, as the hiring founder, interview them against that generic template. So, you hire someone who’s good at being a Sales Manager in the abstract.
Then a few months in, you discover that the actual gap in your business — the thing you needed to fill — is still sitting there, half-filled by someone who’s doing a job that is not actually what you needed them to do. The mismatch doesn’t show up in the interview. It shows up later, quietly, in the form of a hire who seems capable and yet somehow isn’t solving the problem you actually have.
I wish I could say this is an uncommon experience. It’s not. So, when a founder tells me they need to hire someone, here’s the exercise I walk them through. It’s simple enough to do on a single piece of paper.
Take a sheet of paper and draw three columns. In the first column, write down everything you actually did over the past week or month — not your job title’s responsibilities, not what you’re supposed to be doing, but what you actually spent your hours on. All of it: the stuff you’re proud of and the stuff you’re a little embarrassed to admit takes up your time.
In the second column, write down everything you wanted to do, or knew you should be doing, but didn’t have time for. This column is usually shorter (at least a little, hopefully), and it’s usually more revealing, because it tends to be full of the highest-value work in the business — the strategic thinking, the relationships you meant to nurture, you kept postponing because the urgent things in column one kept eating the day. Column two is often where the founder’s actual, irreplaceable value lives, sitting untouched because there was never room for it.
Now look at column one and ask: which of these things would I get rid of, hand off, or stop doing entirely, in order to make room for column two? That list — the things you’d remove from your own plate to free yourself for the work only you can do — is column three.
And column three is the job description. Not a title. Not a generic set of responsibilities borrowed from somewhere else. An actual, specific list of the work that needs to leave your desk so that you can do the work that shouldn’t.
Now, it is important to recognize something: this exercise does not necessarily generate the description of a single position. In fact, column three might resolve into one full-time person. Or it might resolve into two people splitting different pieces of it. It might resolve into a contractor for the parts that are episodic and a part-time hire for the parts that are ongoing.
The whole point is that the exercise doesn’t tell you the staffing structure. It tells you the gap. Figuring out how to close that gap — one hire, several, a mix of employees and contractors — is a separate decision, made after you know what you’re looking for. Founders who skip straight to “I need to hire a person for this title” are answering a staffing question before they’ve finished answering the more basic question of what, precisely, needs to stop being on their own plate.
There’s one more distinction worth making, because it’s easy to lose once you’re actually running the hiring process. None of this means titles are useless. They’re not. A title is a useful piece of shorthand for the outside world — it’s what goes on a business card, what makes a job posting findable, what lets a customer or a partner glance at an org chart and understand who to call. “vice-president of marketing” tells the outside world something real and useful about how to categorize the person they’re dealing with. There’s nothing wrong with using it for that purpose.
What a title is not, and never should be mistaken for, is the actual operating description of the job. The moment a founder starts interviewing candidates, or onboarding the person they’ve hired, against the title instead of against column three, all the value of the exercise evaporates.
You end up right back where you started — talking about “the marketing hire” instead of the specific gap that person was brought in to close and quietly hoping the title and the gap happen to line up. Sometimes they do. Sadly, they often don’t, and the founder doesn’t find out until months later when the person is doing a perfectly reasonable job of being a marketing manager, but the founder is still doing a job they don’t need to do.
The discipline, then, is to keep the two things separate in your own head even after you’ve made the hire. Use the title for the business card, the job posting, the introduction at a conference. Use column three — the actual list of what needs to get done, and what you’re handing off in order for it to get done — for the interview, for the first 90 days, for every conversation about whether the hire is working. If you find yourself describing someone’s job using their title, stop, and go back to the page you filled out before you ever wrote the posting. That page is what you actually meant.
Founders don’t get into trouble because they hire the wrong people. More often, they get into trouble because they hire the right person for the wrong job – a job based on a title instead of drawn from the actual set of tasks that needed to be done. Fix that, and a surprising number of hiring problems that look like personnel problems turn out to have been clarity problems all along.
Iain looked at what happens after that first outside hire arrives in Leadership is hard (Part I): When alignment stops being automatic.