What Should Your Next Hire Actually Fix?

“I just need someone to take a few things off my plate.”

It's a familiar sentiment among business owners, particularly when a company reaches the point where the founder can no longer keep track of everything personally. There's more work than there used to be, employees are coming to them with questions throughout the day, and tasks that should be relatively straightforward seem to require far too much attention.

Hiring someone feels like a sensible next step. And sometimes it is, but I've found that the more useful conversation starts with a different question: What, exactly, are you expecting this person to fix?

Before you start typing out the job description and interviewing candidates, knowing the answer to that question is crucial. A business can hire someone perfectly capable of doing the job and still find itself dealing with the same problems six months later. Often, the issue isn't the quality of the hire; it's that the position was created without a clear understanding of what was going wrong in the first place.

More Work Isn't Always the Problem

As a business grows, its internal operations don't always evolve at the same pace. The processes that worked when a founder had a handful of employees may become increasingly difficult to maintain as the company expands. Responsibilities overlap, information gets lost between teams, and the founder continues to make decisions that other people should be handling.

Eventually, the consequences start showing up in everyday operations. Perhaps customer onboarding takes longer than it should, or projects regularly fall behind despite everyone appearing busy. The founder finds themselves stepping in more frequently and concludes that the team must need additional help.

Consider a company where clients regularly experience delays after signing their contracts. The founder is spending more time than they'd like responding to follow-up emails, and the service team insists they're doing everything they can to keep up. Hiring another administrator seems like an obvious way to relieve some of the pressure.

But on closer inspection, the delays aren't primarily caused by the volume of work. Sales is handing off clients without consistently documenting what was promised, and the service team sometimes discovers those commitments only after the client follows up. There's no agreed process for resolving missing information, so the founder gets involved whenever something goes wrong.

An additional employee might help keep track of outstanding requests, but they'll still be working within the same unreliable process. Before hiring, the company needs to establish how those handoffs should work and who is responsible for making sure they happen. Once that's addressed, it may become clear that additional capacity is genuinely needed; alternatively, improving the process could remove much of the workload that prompted the hiring discussion.

That's a distinction worth making early, especially when the alternative is spending months recruiting and training someone who ultimately inherits a problem they have little authority to solve.

A Capable Hire Can Only Do So Much Without Authority

One of the more frustrating situations for a business owner is having employees who appear unwilling to take initiative. They want someone who can anticipate what needs doing, make sensible decisions, and handle responsibilities without asking for instructions at every turn.

Yet I've learned through managing teams that initiative is heavily influenced by the environment people work in. An employee might be perfectly comfortable making decisions within their area of expertise, but if those decisions are regularly questioned or overturned, they'll eventually start seeking approval instead. It's a rational response to how they've been managed, even if it creates more work for everyone involved.

Now imagine bringing a new executive assistant into that environment. The founder wants someone proactive who can manage competing priorities and take work off their desk, but continues to review every outgoing message and insists on personally approving routine scheduling changes. Before long, the assistant is spending a considerable amount of time waiting for instructions, while the founder wonders why hiring support hasn't made much difference.

The assistant may be capable of far more than the role currently allows. Unless the founder is willing to establish reasonable boundaries for independent decision-making, replacing that person with someone more experienced may produce much the same result.

This is where I think business owners sometimes underestimate their own role in successful delegation. Assigning someone a responsibility is relatively easy; giving them the information and authority to manage it properly requires more deliberate effort. Oversight is still important, particularly when decisions have financial or reputational consequences, but it shouldn't become a requirement for approval at every stage of ordinary work.

Sometimes You Really Do Need Another Person

Of course, not every overwhelmed team is dealing with a structural problem. There are businesses with well-defined responsibilities and effective processes that simply have more work than their current employees can reasonably manage. If demand has increased and the team is consistently operating at capacity, bringing in additional support may be the appropriate decision.

There are also situations where the business has developed needs that nobody on the existing team is equipped to handle. An experienced executive assistant might be invaluable to a founder whose professional commitments have become increasingly complex, while a growing company struggling with coordination across departments may benefit more from operational leadership. For repetitive activities governed by clear rules, improving the technology or introducing automation might accomplish more than creating another administrative position.

These are different investments, and the fact that each could make a founder's life easier doesn't mean they should be treated as interchangeable.

The point isn't to discourage hiring or insist that every business problem can be solved by improving a process. It's to understand whether you're paying for additional capacity, expertise you don't currently have, or someone to take responsibility for work that already has a clear purpose. If you can't explain what the new person will be responsible for achieving, there's a good chance the role still needs some serious thought.

What Needs to Change Before Someone New Arrives?

Before committing to another hire, I'd encourage founders to look closely at a few recent situations that required their unexpected involvement. Choose an actual problem rather than relying on a general feeling of being overwhelmed, and trace what happened before it reached your desk.

If a client complained about a missed deadline, don't begin with the final email you had to answer. Look at when the delay first became apparent and what prevented the responsible employee from addressing it. Perhaps the deadline was unrealistic from the outset, or the employee was already managing more work than anyone had accounted for. You might discover that the real obstacle was simply that they weren't authorized to adjust the timeline without your approval.

Each explanation points toward a different response. A capacity issue could justify another employee, whereas unclear authority may be something you can resolve with the people you already have.

The exercise isn't intended to become another elaborate project for an already busy founder. It's a way of making sure you're responding to evidence rather than frustration, and it can help clarify what needs to happen before someone new joins the business.

I would also pay attention to how the proposed role is being described. If the job description is essentially a collection of everything the founder no longer wants to do, it's worth asking whether those responsibilities actually belong together. A talented employee can take on a varied workload, but they still need a coherent role and a reasonable understanding of what success looks like.

While that clarity certainly matters for the business, it matters just as much for the person being hired. Someone joining a company should have a fair opportunity to succeed rather than discovering that they're expected to compensate for problems nobody has addressed.

Set the Business Up for the Hire You Actually Need

The best hires can make an enormous difference to a growing business. They bring valuable experience and create room for the founder to focus on work that genuinely requires their involvement, and that they actually enjoy. Over time, a strong working relationship can change how an entire organization operates and performs.

But the benefits aren't automatic, and hiring shouldn't become the default response whenever something starts to feel difficult.

If the problem is an ineffective process, improve it. If someone already on the team can take greater responsibility with the right authority, give them that opportunity. And if the business genuinely needs another capable person, make sure there's a clear role for them to step into.

The question isn't simply whether you can afford to hire someone or how much work you could hand over. It's whether you've identified what needs to improve and created the conditions for that person to contribute meaningfully.

Your next hire shouldn't have to be the one to figure out what they were hired to fix. Don't make your lack of clarity their responsibility (unless that's exactly what you're hiring them to do).

*Join me on November 19 for my YEC session, The Right-Hand Hire, where we'll take this conversation a step further. We'll explore who to hire, when the timing makes sense, how to find and work effectively with the right person, and how to recognize when a different solution might serve your business better.*