He’s a wonderful guy – he just needs a little more technical training to get him up to speed.

I can see so much potential in her – if only she could develop some better habits in her phone manner when talking to our customers.

I just wish I had more time to devote to coaching and supporting my team. Any lacklustre performance is on me – I’m the leader.

I know he’s not busy enough right now. We just need to reach this next milestone in our business, and then he’ll be able to max out his capacity.

Can you hear yourself saying these things? You love your people, and you want to build them up and show them their potential. You’ve hired someone wonderful, and you’re finding it tricky to get them doing the right work, for the right number of hours, in a way that makes everyone happy.

Meanwhile, though, you’ve got a business to run – and finite time and resources to support and nurture your people.

It doesn’t come easily to you to view people as “assets”; that feels cold. But you’re feeling stretched thin, under-supported, and you aren’t confident that your team is as effective as it could be. You might catch yourself micro-managing (and seeing bristling hackles in response), withdrawing into over-doing (to compensate for what you can’t seem to delegate easily), or daydreaming about being able to hire your dream candidate (once you’re confident you can offer an attractive package to someone who can afford to be choosy).

These are all signs that you’ve got a poor fit between the needs of your business (and by extension, you) and the capacity of your team.

So: How do you close that gap? Do your people need training (or coaching, mentoring, or simply more time and experience)? Or do you need to let them go (or rework their role so you can hire more support)? How can you tell if your (wonderful, perfectly imperfect, potential-filled, and perhaps beloved) people are going to give you a solid return on your financial investment?

(Did you catch that word: financial? I slipped that in because it’s critical that you recognize the financial implications of having someone on board who is costing you time and energy while they’re ramping up. The hours you spend with them, and the hours they spend learning new skills, are costing you in the same way it would cost you to send them off to a training course. So you must weigh your decision here against those costs.)

You can start by asking these questions about your business, yourself, and the person (or people) who is causing you the most concern:

  • Where do you need support from your team right now? What are the missing pieces?
  • What tasks do you long to delegate, but can’t seem to find a way to hand off?
  • What is that tricky team member best at? How well does that strength connect with the needs you’ve identified? 
  • What skills are they lacking? What resources and support are readily available to you? (Think classes and workshops, books, self-directed learning, mentoring and job shadowing, and so on.)
  • If they decided to resign today, would you fight to keep them? If so, why?

Why Training Doesn’t Always Work

It’s much easier to teach someone new skills – be they learning your way around new software, or sales techniques – if they are seriously interested in learning them. (Leading horses to water, and all that.)

That doesn’t mean they need to identify as a sales master in the raw, but it does mean they must be able to see the value in the training, and willing to commit to learning. If they don’t check those two boxes, you have a bigger problem on your hands, which is that your team member’s interests diverge from yours and your business’s. That on its own doesn’t mean you need to let them go, but it does mean you need to assess very carefully whether a) they are the best possible fit for the role they want to have, and b) whether your business can afford to accommodate their preferences.

For example, if your business is creating websites, and you have a designer whose true love is letterpress design, it may be an uphill battle to get them to hone their digital design skills – and unless you’ve got a client base that’s interested in taking their digital ideas to print, you may simply not have enough work to keep her busy with the stuff she loves most. The result is an unsatisfied employee, a business that’s struggling to compensate for that employee’s lack of passion, and a boss (that’s you) who’s distracted from the things that matter most by managing all of this.

Let me lay that out for you a different way:

There’s an opportunity cost to your employee here: They are spending time trying to get better at something they don’t actually want to do. They could be off somewhere else instead, doing the work of their heart – or drilling down in their existing role to the heart of what they love doing, with the likely result of reducing their hours.

There’s an opportunity cost to your business: You don’t have the best possible person in the role, which means quality of work is suffering. 

And there’s an opportunity cost to you, because you are doing management work you don’t want to be doing, filling in the gaps your team member is creating, and leaking productivity by stressing about this. 

See how that perpetuates unhappiness all around?

There is room for compassion here, for them and for you. You want the best for your people, and sometimes the best thing for them is encouraging them to do the work they love, elsewhere – or giving them the option to reduce their hours so they are only doing the work they love most for you, and freeing you up to find the support you’re missing right now.

If you have a voice in your head telling you it’s selfish to want your team to be highly engaged in the work you’re paying them for, try asking yourself how you’d want to be managed if you weren’t enjoying your work. Chances are, you’d jump at the opportunity to focus on work you actually enjoy.

When is Mentoring in Order?

This is not to suggest that mentoring and training don’t have a place, of course. Everyone needs skills development, new challenges, and growth opportunities.

So long as you feel confident that your team members have the core qualities, aptitudes, and interests that align with their roles (and your business’s needs), it is your responsibility as the team leader to help them identify and acquire the skills they need to develop further.

What I’ve noticed is that there is a significantly different texture to mentoring an employee who fundamentally clicks, versus one who doesn’t jibe with their role. Even if there are skill gaps, when things are clicking at a general level there’s far greater energy and momentum; there’s a “yes, and” feeling, as in “Yes, you’re doing great with this – and I’d love to see you take this on as well.”

In cases where there’s a deeper disconnect between a team member and her role, I’ve found that requests for further mentoring or training can mask a desire for a different role altogether – and when that’s the case, you need to ask yourself honestly whether your business can accommodate such a role change (be it a significant jump in responsibility, a change of focus, or a scheduling issue).

To find out which scenario you’re looking at, you can:

  • Welcome training and mentoring requests with a couple of rounds of “Why?” – as in, “What’s interesting to you about that?” or “Why does that appeal to you?” – to dig deeper into their motivations and interests.
  • Notice what work gets done quickly, and which assignments drag: They’re a clue to your team’s passions.
  • Reflect on your level of enthusiasm for offering skill-building support. If there’s resistance, what is it?
  • Crunch the numbers. What would you be willing to spend to hire someone with the skills your team member lacks? What is the cost of providing the training they need? (Include the cost of your time, as well as hard costs such as tuition and paying for their time while they attend training.) What is the value of these skills to your business? Can you parlay them into new offerings?

My approach has always been to hire for intelligence, shared values, and a certain X factor I’d describe as somewhere between friendliness and engagement (i.e. do they seem keen and approachable?) – and train for technical skills if necessary. I’m also a strong proponent of hiring the most senior people you can afford, especially when you’re running a small business, because odds are good you can’t afford to spend your own time training people up. I’ve never regretted making a senior hire, even when their compensation package made me sweat a little. Senior people cost a little more, but they bring both peace of mind (because your business is in good hands) and enormous added value. Junior team members, on the other hand, will require more of your time and energy – and that’s okay sometimes, but you need to be aware of it and ready to invest in them.

What pains me is seeing entrepreneurs who know exactly where their energies should be focused, but who are caught in a cycle of devoting huge amounts of time to supporting (or compensating for) employees who aren’t pulling their weight. If that sounds like you, I encourage you to get clear on the value of the support you’re providing, the cost to your business, and what you’re missing out on by not having your dream team. It’s too easy to fall into the trap of thinking “This needs to be done, so I’ll just do it.”