Struggling to train someone on a delegated task?

Finally, you found someone to replace you and perform a specific task. Maybe it’s even a task that you never liked doing and you cannot wait to get this off your plate.

You set up a meeting, start training the person, and then… you find yourself wanting to nudge them aside and take over.

You feel they’re not doing it right. You try to explain. You demonstrate. But nothing seems to be working. You’re tempted to just forget the whole thing and take the delegated task back.

Will that really serve you?

Unlikely.

So what can you do when struggling to train someone on a delegated task?

Was the task the right one to delegate?

The first thing to look at is ask yourself was the task the right one to delegate? Sometimes there's this desire to get rid of tasks because we don't like them. It's something that we can't stand doing. It's something that drains us. It's something that we drag our feet on because it's just miserable. And we try every trick in the book, “Okay, as soon as I have that done, I'll be able to move on.” And still, we can't seem to be able to motivate ourselves. We know we have to do it, so we eventually do it, but it's just absolute torture the whole way. So those are the ones that we tend to be like, “Oh, get rid of this. I can't stand this.” And we pick those to delegate. But it doesn't always make sense because those are not necessarily the right tasks to delegate.

Have a look at the impact that the work has. Think about, should there be a mistake, would the consequences be dire? Could you lose a client? Could your revenue be halved? Could you potentially even put your whole business at risk? Those would not be good things to delegate.

If it's just a question of, well, it would be embarrassing, but it would be excusable, then that we can live with. You really want to make sure that what you're delegating doesn't only come from a place of frustration. It doesn't mean that the two don't go hand in hand, but make sure that it is something that, should there be a mistake, it wouldn't be something that would be overly detrimental to your organization. I would hesitate to fully delegate that unless you are very sure that the person can truly execute it masterfully.

As part of this exercise of reviewing, whether it's a task that should be delegated in the first place, does this task require too much of your review and approval before they can accomplish it? Because if you spend more time reviewing and approving than actually doing, and that's consistent, not just because they're new and it's the first time or the first two times or the first three times, but if it will continuously require this level of involvement, maybe we can look at delegating something else. Why would you want to spend more time doing that? Or even if it's equal time, maybe you should look at something else.

Even if it's something that you really don't like, maybe there's something else that they could be doing that would advance the business better. So that may not be the right task. One way to verify whether it's the right task to delegate, is to write out how to perform the task step-by-step and then watch them follow the steps. Is there a lot of information that you know that isn't being shared? If it's just a case of “Okay, I need to trade them a little bit.” That's one thing. But is this information that would take someone years to gather and they don't have it? Then that might not be the right task or it might not be the right person. Look at that, consider whether that was the right task.

Also, think about how sometimes we are so knowledgeable about something that we forget what it's like when we started and we take that information that we know for granted, and a new person wouldn't know that. Is it really that or is it that the task itself is that complex and it really requires someone who masters this type of work and therefore may or may not be appropriate to delegate depending on who's doing it.

But before we move on to that, just consider all those elements to see whether it's something worth delegating. As part of that effort, consider if it can be broken apart. Maybe there are certain steps that are appropriate to delegate, but not the whole thing. Even if you can have some support for some of those steps, maybe that would be worthwhile.

Are they the right person to take over the task?

I kept coming back to how the task itself, whether it's appropriate to delegate, and this is very closely tied to this second point: to evaluate whether they are the right person to take over the task.

Depending on the budget, you may have had to hire someone with less experience. And maybe this task absolutely requires someone who has deep, deep, deep knowledge, especially if it's a task that has a huge impact on the organization, if it has legal implications, if it has people implications, if it has revenue implications, you want to make sure that whatever task you're delegating is delegated to someone of the appropriate level. One of the reasons you might be struggling in training this person is maybe they don't quite have the level of training that they need to be able to do it. And is it a question of, “Okay, I'm just going to train them a little bit and then they'll be able to do it?” Or is this going to require significant training for the person to be able to do it? Then it might not be the right person.

A couple of things that might be a good indication that it won't take long to train somebody up is if it's a tool. Usually tools can be learned pretty quickly. So if it's that, typically they'll pick it up fairly quickly. If it's knowledge of the company itself, usually that gets picked up pretty quickly also. And if it's how the task ties into the rest of operations or client services, again, that can be fairly easily explained. You can ramp up someone pretty easily in those cases and get them to productivity and doing the task at the level that you would like it to be done fairly quickly.

Another aspect to evaluate when you're considering whether this is the right person is whether they are channeling the values and mission of the organization while accomplishing the task. Because if they're not embracing that or channeling that as they're doing the task, maybe it's influencing how they're doing it. And maybe that's why they're falling short because they don't fully grasp the approach that the organization takes to accomplishing certain tasks. If that's the case, maybe you just need to explain the mindset behind how to accomplish the task, and maybe that'll ramp them right up. Maybe a lightbulb will go off in their heads, “Oh yeah, okay, I get why my approach isn't quite what it should be.”

Another thing to consider is that perhaps you just need to explain why this is so important and the consequences and risks associated with the way that they're accomplishing the task as you're training them.

And if you see that they're doing something completely different and you're like, “Okay, the reason we don't do it this way is because…” instead of just saying, “No, do this this way.” this will help them know why. If we take that extra moment to also explain the how and the repercussions of the approach, then that could help them truly understand. And then if they fully grasp the context, then that may change their approach to the task and then get it to where you were hoping to, and maybe that would help with the aha moment that you're hoping for and unlock that training.

Were you secretly wishing for your clone?

The third piece to consider, and you may not like this one, is were you secretly wishing for your clone? I've been guilty of that one too!

Sometimes, we just wanted a clone of ourselves. We just wanted another “me”. And if you're going to delegate something and you're trying to train someone and it's not quite working, maybe you need to recognize that this person is not you. And so maybe you did hire them to be similarly-minded of a certain level of aptitude and experience. They may even remind you of yourself, which is why you like them so much, but they're still not you. They are a different person and therefore they will accomplish things differently.

And there will be nuances that are going to be different. You have to recognize and accept that. And as part of my recruiting course, that's something that I was talking about, how sometimes you're looking for a clone of yourself, but that clone is still not you. And it's really someone who has similar experience, similar mindset, similar approach to things, but you have to recognize that it won't be exactly as you would have done it.

Assuming that you feel that the task was the right one to delegate, that this person is the right person, then you have to let them do it their way. Of course, I fully recognize that sometimes there is no room for interpretation. It's either right or wrong. I'm going to say probably in legal cases, probably in accounting, there are probably times when it's right or it's wrong. You do this or you don't. And most of the time there's not much room for interpretation there. Maybe that's the case in the task, and maybe that's why they need to follow it exactly. But if it's something that's that specific, they normally would've had some form of training.

But if it's something that could be picked up quickly by most individuals, then make sure that the steps are very clear. And I would say even if it's something that doesn't need to be done, exactly still make sure that all the steps are clear. Make sure that they understand each and every step because maybe part of the reason the training's not going very well is because things are clear in your mind but not so much in theirs. If you make sure that they understand every step, then you might unlock where the training's actually going wrong. And if there is room for them to be themselves, then let them be.

If it's too hard to watch, if it's making you cringe to watch them, and it's possible to do so, wait to see the results. Maybe you don't watch them perform it. Maybe you wait until they come up with the result and you evaluate that. And then once you evaluate the result, then is it what you wanted to see? Maybe yes, maybe not. And then you take it from there. But consider possibly just letting them be and seeing what they come up with.

Now, if there is a risk involved, for example, if it's something that's going to a client, make sure that you review it before it goes out. I'm pretty certain you've already determined that you'd be doing that, but I still feel better mentioning it. So make sure to review it before it goes out.

Assuming you try all these things and you still find yourself unable to let go and let them do things their own way, or you're struggling to provide feedback that doesn't involve you overhauling what they're doing, ask yourself whether there's someone else who can train them.
Maybe normally you are the person who trains them, but you know what, this time it's not quite clicking the way it should be. So maybe there's somebody else on the team who is doing it who could teach them, or somebody else who maybe hasn't done it in a while, but reading your list of steps could accomplish it, no problem. And take this new person through how to do it.

And if there isn't and you're it, then work on recognizing that you hired them for a reason and try to focus on building trust in their capabilities.

Try various approaches

Just because someone struggles to pick up what you’re teaching them doesn’t necessarily mean that you’re an inefficient teacher.

It could be that your learning styles are different. Some learn by watching, some by reading, some by listening. I try to hit all of these and incorporate doing as well.

My preferred way, the one I’ve found the most effective, is teaching someone by showing them how to do it and recording the teaching session so that they can view it later. Then I ask them to write out the steps as they understand it. I then plan a second training session where I watch them do it while I review the steps they wrote out. I modify the text based on how it goes and what I consider to be missing information or needed clarification. The third attempt is by themselves and I review the result.

Typically, by then, they’re able to do it.

By considering all these various aspects, you should be able to pinpoint where the breakdown is occurring and address the core training problem. And, finally, be able to truly delegate this task.