Using One-on-Ones: Informal Task Deep Dive

Actions to take: Occasionally use your one-on-one time to get a deep understanding of one of your employee's tasks. Have a plan to begin asking about the task when the opportunity presents itself. Ask open-ended questions that convey your enthusiasm and eagerness to understand their work and how they do it. Afterward, mentally review the conversation for potential follow ups.

To be a truly effective boss, the most important thing you can do is build a trusting relationship with each employee. By far the easiest way to do that is through routine one-on-one meetings. Better-boss.com recommends that those meetings are scheduled, 30 minutes, weekly, and rarely missed, with the first half of the meeting spent on whatever they want to discuss and the second half for whatever you want to discuss. All posts about one-on-ones assume this strategy.

One of the most difficult things about managing others is getting a clear picture of how employees do their work. It is hard enough getting an accurate understanding of what your employees are doing all day. (Though we will assume that readers of this blog have gotten over that hurdle with the help from our one-on-ones basics series.) Even if you sat and watched an employee work all day (not recommended), you wouldn't get much understanding of how they do their job. This is obviously true for white-collar jobs where the work looks like "sit in front of a computer all day." It is still true for blue-collar work, however. My first jobs were dishwasher, then short-order cook. In both of those positions, I was constantly making decisions, big and small, about how best to get the job done. Those decisions, and the factors I considered to make them, are invisible. You would only get a true sense of how I did the work by interviewing me about it.

Which is exactly what bosses should be doing with their employees on a regular basis. When you gain a sense for how your employee does their work, there is a goldmine of benefits:

1. Opportunities for feedback. This is the most obvious benefit. As you discuss the finer details of their work, you will naturally notice places for feedback. They will say something clever, and you'll want to encourage them to continue that good practice and potentially port it over to other areas of the job. You also see places where they need to abort some element of their process or add to it. For instance, a deep dive into a task that involves other team members might reveal that the employee doesn't think to inform their coworkers when their work might be early or late. There is an easy place for a little corrective feedback.
2. You will discover best practices to share with all employees. If you have four people who do a thing, one of them does it best. You'll learn who it is by doing a deep dive into that task with all four. That one person might do the work so much better that it is an obvious win to have everyone start doing it that way. 
3. You will learn more about your employee's communication style. One-on-one agenda items tend to be brief and obvious—answer this yes/no question, tell me the status of this project, find out questions about some upcoming change, etc. Having a more open-ended conversation affords the opportunity for a slightly different kind of communication. You will find that you understand your employee a little better after doing a few of these deep dives.
4. It is useful for professional development. When you interview an employee about one of their tasks, yes, you'll learn about that task. Just as importantly, you'll learn something about their broader skillset. Hearing how they do their work will help you understand your employee's strengths, especially if you do this with two or three tasks over time. You'll recognize patterns. Your detail-oriented people will have a dozen steps related to planning and ensuring that things don't fall through the cracks. Your big-picture thinkers will talk to you about the way they develop their ideas. This new knowledge will help you both have conversations about future career decisions and skills the employee should focus on.
5. Employees will feel that you are attentive (in a good way). Yes, attention from the boss is a thing that we avoid most of the time. There are some contexts where it feels good to shine a light on your work. People are generally proud of their work, especially the parts that involve independent decision-making. When you do this right, you might hear an employee say something like, "You know, I've never had a manager who wanted to learn my process before."

Now that I've (hopefully) convinced you that this is worth doing, let's talk through the how-to. There is really not much to it. The only real trick is starting the conversation naturally, in a way that doesn't catch your employee off guard. 

Wait until the subject comes up. You may need to wait through several one-on-ones. With most of your one-on-one agenda items, you put it on your list and bring it up when you're done talking about the previous item. This is a little different. We want to make this conversation feel light and informal. If you abruptly cut to a conversation about one of their tasks and rapid-fire questions, a couple things will happen. Your employee will feel put on the spot and nervous. They'll assume they did something wrong or there is something wrong with the task itself. They'll feel blindsided, like you are pulling something on them by not letting them prepare for this conversation in advance. By waiting for the topic to come up naturally, you can avoid all this. You can simply show enthusiasm, ask your first question, and give the employee plenty of space to answer before you ask your next question. They might think it a little odd, but done right, they'll just think you took an interest in their work. 

The only other tip is to prepare in advance. Know what task you want to learn more about. Prepare three or four open-ended questions you will ask. Mentally picture that first question. For instance, you might have an employee who is responsible for answering emails sent to the customer feedback account. Next time that task comes up, you could be prepared to say, "Oh! I've always wondered what the breakdown is between people saying nice things and people complaining. What's it like?" This can very easily transition into you asking questions about their strategy for responding to complainers. The conversation goes from there.

The average boss barely understands what their employees do all day, and they have absolutely no clue how the employees go about their work. Better bosses take the time to show interest in the details. Integrate informal task deep dives into your routine for one-on-one agenda items. Try it with three or four employees, and you will quickly discover the benefits of taking the time to understand how your employees operate.