How to Develop Your Team's Skills Through Coaching

Many managers relegate training to ad hoc group sessions, but these are often too generic, too theory-heavy, and too detached from day-to-day application to be effective. Instead, training is most effective when delivered one-on-one, through coaching.

Similarly, managers often relegate training to a mix of company-wide subject-matter experts, HR department trainers, or external consultants. This only works when the specialist trainer has a deep knowledge of the work done by the team they train; otherwise, their training will also be too theory-heavy and too detached from day-to-day application to be effective. Instead, training is most effective when delivered by the team’s supervisor (assuming they are trained to do so).

The point is, skills are trained better through the people who supervise the work, rather than through the events that interrupt it.

Group training is good for introducing standards, but coaching is necessary for installing them into behavior.

Why training events do not build capability

Large training sessions have their uses. They can orient new hires, spread a shared vocabulary, or raise awareness of a risk everyone needs to know about. They can be effective for matters such as compliance. The problem is that group sessions transfer information, not skills.

That’s because, to improve someone’s skill, a trainer (or a training document) must fulfill three requirements:

1. Meet them at their current level
2. Discuss relevant tasks
3. Provide feedback

These are extremely hard to do when dealing with more than one or two people at a time.

Point (1), meeting people at their current level, can be partially fulfilled in a group setting by pre-selecting participants so that they are of roughly similar skill. Even then, two problems are common. First, not everyone at the same skill level on paper is actually at the same level. You may think that a group of new hires from college is at the same level, but they probably are not. Second, not everyone who starts at the same level remains at the same level halfway through the training. Some people are simply faster learners than others.

Similarly, point (2), discussing relevant tasks, can be partially fulfilled by pre-selecting participants who work similar jobs. But even then, not everyone who shares the same role on paper shares the same tasks, performs them with the same frequency, or does them the same way. This is particularly relevant when people share the same role across different offices, countries, or business units.

Finally, point (3), providing feedback, is probably the hardest to deliver well in a group setting. Either only a small percentage of participants receive in-depth feedback, or all participants receive very shallow feedback; either way, most participants will be left with unanswered doubts and unclear minds.

So, if you want to build skills, do not use group training as the main mechanism; instead, use one-on-one coaching.

Who should provide this coaching?

The second-best answer is a subject matter expert, internal or external, using one-on-one sessions.

The best answer is the team’s supervisor, and not during ad hoc one-on-one sessions, but on the job, or during naturally occurring operational interactions.

The obvious objection is that the supervisor is often less skilled at coaching than a top performer or an outside expert. That is true, but it does not change the conclusion. The expert wins on coaching skill, whereas the supervisor wins on frequency, on knowing the actual tasks and constraints, and on being present when the next attempt happens.

This also answers the case where the supervisor is not the most skilled person on the team. You do not need the supervisor to be the best at the task. You need them to be able to provide feedback and answer doubts. If you think about it, sports coaches are often worse players than those they coach, but that doesn’t preclude them from coaching — what matters is watching people perform and being able to give them feedback.

Of course, this does not mean every supervisor is automatically a good coach. If an organization wants the capability to grow, it must make supervisors capable of coaching: giving them clear standards, examples of good and bad work, time to review real work, and calibration with other supervisors.

Capability is built by supervisors who coach

Before we continue, let me clarify what I mean by coaching. I do not mean motivation or accountability, or at least not only that. Those help when motivation is the bottleneck, but usually it is not. Most often, the bottleneck is a missing skill or missing context, and closing that gap requires someone who understands the work well enough to teach it.

A supervisor who coaches does a few concrete things: they give specific feedback, they teach what separates bad work from good work and good work from great work, and they run role-plays and hypotheticals so people can practice before the stakes are real.

Here are four frameworks that can help:

• Bad, good, great. For a given task, spell out what a bad performer does, what a good one does, and what a great one does. This turns a vague standard into something a person can aim at.
• Enough, too little, and too much. When you delegate, describe what a finished task looks like, what would be too little, and what would be too much. Do the same when reviewing work.
• Always explain the why. Always explain the reasoning behind your decisions and your feedback. If you don’t, they will guess. And if they guess wrong, they will think your decisions are arbitrary and your feedback subjective.
• Role-play and hypotheticals. Ask what they would do in a situation and give immediate feedback, so they find their mistakes in a safe setting rather than in high-pressure, high-consequence circumstances.

Coaching also tests the manager’s own standards. If you cannot explain what better work looks like, you do not yet have a standard; you only have a preference.

One warning before you start: bad coaching is worse than no coaching. Vague feedback, feedback that contradicts last week’s, or correction with no reason attached, teaches people that your standards are arbitrary and that effort is a gamble, and they respond by hedging, hiding work, and waiting to be told. So, ensure that your coaching explains the reasoning behind your feedback and remains consistent.

The coaching loop

The coaching loop consists of observing real work, comparing it to a standard, picking one improvement, explaining the reason, letting the person try again, and reinforcing the next correct attempt.

Feedback must be immediate, or close to immediate. If the person was given some feedback yesterday and improves today, not being acknowledged for the improvement will send the message that it didn’t matter, and the response will be disengagement from the task and/or the coaching.

None of this has to be extra work layered on top of the job. Coaching is a reallocation of interactions you are already having, not a second job competing with them. You already review work, answer questions, and sit in the same meetings. Coaching means doing it closer to where and when the work takes place, and explaining the reasoning behind your feedback.

I repeat: coaching should result in less work for managers, not more. When a manager says they lack the time to coach, it’s usually because they spend a significant part of their week “putting out fires,” correcting mistakes and misunderstandings, and doing their subordinates’ jobs. But not only are these downstream of a lack of coaching (if the manager spent a bit more time coaching, there would be fewer problems to correct), but these are also opportunities to provide coaching at little extra time cost.

Build competence before you expect a habit

A common mistake is to ask for a new behavior and expect repetition alone to make it stick. It will not, if the person cannot do it well yet. A behavior becomes a habit only when repeating it isn’t too tiring or frustrating, and that usually requires a baseline of competence. (More on this in my previous essay, Incentives can buy more of a behavior, but rarely create it.)

Consider a salesperson told to improve conversion by asking more questions on calls. During the training, everything sounded clear. But on the first real call, she does not know which questions to ask, feels awkward, and asks weak ones in an uncertain voice. The call goes badly. What gets reinforced is not the new habit but the urge to avoid it.

Failed early repetitions teach the person that the new behavior feels awkward, risky, and unrewarding, so they start avoiding it before it ever becomes a habit.

So, before pushing for more repetition, make the behavior easier to do well. Lower the difficulty of the first attempts, give structure, teach the principles behind the behavior, limit the number of things to hold in mind at once, and make early feedback immediate and useful. A beginner does not need more pressure; they need the first few reps to succeed.

Repetition, feedback, and reinforcement

Once someone can do a thing competently, three levers turn it into a habit.

The first is repetition. Keep asking the same question until it becomes the question they ask themselves. A manager who asks “Is there any way we can do this faster or cheaper?” in every review eventually instills that question in the team’s heads.

The second is feedback. If someone asks a question or surfaces a problem and gets ignored or blamed for it, they will learn that the next time they have a question or see a problem, they should pretend everything is fine.

The third is immediate reinforcement. If you ask someone to learn something, and they learn it, and you don’t notice, the lesson they will take is that the next time you ask them to do something, they should put less effort into it. This is not just a question of feeling seen; it is also that not noticing that something got done signals it was not important.

Case study: coaching better emails

Let’s put into practice what we have seen so far with the help of a concrete case study: coaching someone to write clearer emails.

Instead of announcing a training, wait until an email with clear room for improvement lands in your inbox. In your next one-on-one, mention it and pick one thing to fix, not five. If the email was not concise, do not just say “be more concise,” because they probably believe they are already concise, by their standards. Instead, show them your standards: put the email in front of them and ask them to strike out everything unnecessary, then confirm that what is left reads more clearly. Finally, watch the next few emails, and when they get it right, let them know you noticed.

That small loop, observing, teaching one thing specifically, letting them practice, and reinforcing, carries the same principles we just saw: competence before habit, repetition, and immediate feedback.

(You can find my full guide on email coaching, with exercises for conciseness, clarity, and directness, in How to coach your team to write more effective emails.)

Track growth with soft metrics, discussed often

Many managers rely on hard metrics to track performance, such as contracts signed or invoices processed, but soft metrics are often more useful than hard ones when it comes to building skills. Take a basketball player who struggles to score. A hard metric like points per game helps only if the limitation is effort, but if the problem is shot selection, that target pushes them to take worse shots to hit the number. A soft metric like “shot quality,” discussed after games, addresses the actual skill gap.

“But Luca, soft metrics are subjective.”

That’s only a problem if you do not discuss them frequently. Do it only once a quarter, and you may create defensiveness and disagreement. But if you discuss them frequently and informally, say at the end of a one-on-one on another topic, it produces an open, constructive conversation. Plus, the more you discuss them, the more your subordinate’s judgment of soft metrics will match yours.

There is no need to pretend soft metrics are objective; instead, anchor them in examples: “This is a weak customer update, this is an acceptable one, this is a strong one, and here is why.”

These metrics also help you get feedback on your coaching itself. If your coaching is working, the soft metric should be moving: the customer updates getting sharper, the questions getting better. A soft metric that does not move after weeks of coaching is telling you something, either that the coaching is not landing or that the gap was never skill in the first place. The trajectory of the soft metric is how you know whether any of this is working.

(More about soft metrics in my old essay, How to use soft metrics to develop your team’s skills.)

What about AI?

Remember the three requirements that made group training tricky (meet people at their level, work on their real tasks, and give feedback)? They were hard because they did not scale. A human coach can deliver all three, but only to one or two people at a time. AI can help relax this constraint.

Beyond automating tasks where it makes sense, AI can act as a training and quality system: it can review a sample of outbound work against your standards, flag what is missing, and suggest improvements, giving people immediate feedback until the standard becomes a habit. It meets each person at their own level, on the specific task in front of them, with feedback delivered the moment the work is done, and it does this for everyone at once. The three requirements that were impossible to satisfy at scale become cheap.

For example, if a manager has defined what a clear customer-update email looks like, AI can review drafts against that standard, flag missing context, ask whether the recommendation is explicit, and suggest a tighter version before the email is sent.

You can also have your best performer codify what they do into a reusable standard that the tool applies for everyone else, which raises the floor toward the level of your strongest person. This is the same move as having a supervisor coach against an expert’s standard, run at the scale of the whole team and at the speed of every draft.

That said, AI should only complement a supervisor’s coaching, not replace it. AI can provide the repetitive, scalable part of coaching, checking work against a known standard and returning immediate feedback. But a human is needed to set the standard in the first place, judge the work AI never sees, coach the things that have no written rubric, and decide what is worth getting good at.

(More on this in my essay Automation vs upskilling.)

Conclusion

Skills and capabilities aren’t built with group training sessions, but by supervisors who coach on real work, build competence before expecting a habit, reinforce the right behavior with repetition and feedback, and keep skills visible through frequent, low-pressure conversations.

If you want help turning this into how your organization develops people, diagnosing where skills stall, training your managers to coach, and setting up the metrics that track growth, that is one of the things I do professionally. Here is how to start.