Time management skills: The check-in

Time management skills

Here’s an interesting little dichotomy around time management skills. Many people don’t have them, but they’re essentially crucial to projects and deliverables actually being achieved at work. As such, it brings up one of the great managerial questions. See, time management skills should be something that a person develops organically, i.e. on their own. But if you manage a person with terrible time management skills, what’s your responsibility to the process? Their lack of time management skills is probably hurting you in some way, so do you attempt to manage them up in terms of a competency they lack? Or do you find other ways around it?

Phrased another way: how much of being a manager is developing these so-called ‘soft skills’ in your employees?

In my mind, leadership is all about developing these soft skills — but unfortunately, most bosses I’ve ever seen will instantly bellow, screech, and yelp when something isn’t perfect the first time (totally forgetting that failure happens every day) and rush to HR looking to put someone on a ‘performance improvement plan,’ which as we all know is code for: ‘Get em out.’

But maybe there’s a simple way to improve your subordinate’s time management skills.

Time management skills: Where does the problem lie?

I’m about to blow your mind, so get ready. Are you sitting down? OK. Let me explain to you the one major principle that allows most of work to exist the way it often does. Ready?

No one knows how long anything takes.

This literally explains everything about work. Let me give you a few examples quickly.

I was at a wedding last year and talking to this girl who works in marketing for a big credit card company. She probably makes about 3x what I do in a given year, no joke. She was explaining her job and I didn’t really understand it; she was saying something like, “If a partner calls and has a complaint or issue, I record that on a spreadsheet.” I was kinda buzzed, so finally I just said, “Is that really a 40-hour/week job?” She laughed and said “Sometimes, but most of the time it’s about 27. But I have a baby now, so I always tell people it’s 65 hours/week. No one really knows how long it takes.”

Story II: I once worked with a lady and her primary job was to take something already published and send it to someone in Australia to be republished there. Essentially, a middle person in a process. She didn’t do anything to the thing that was published; she just PDF attached it and sent it to someone else. This was her primary job, mind you. Job role and definition is a joke at most companies. So, how long would you estimate this takes each week? Like 3 minutes? Maybe 10 minutes if the PDF is large or something? She was always telling people how slammed she was, right? No one knew what to do, really … “That work doesn’t seem hard … it seems like I could give her more work … but maybe I don’t know … I don’t know how long things take…”

See, the whole deal where no one knows how long anything takes allows so many people to hide behind “I’m so busy!” because it feels good to say that — it makes you feel high — and who the hell is gonna question you? They don’t know your process, baby!

This brings me to a recent Fast Company article on time management skills. Here’s a key section:

The most common skills gap, though, is being unable to estimate how long things take, and from that, planning back from a big deadline. People can manage multistep processes in some parts of their lives—”It’s like putting bread in the oven,” Tulgan says—but not others. Indeed, time estimation for work projects is a skill that very few people ever truly master (see “How To Manufacture More Time In Your Day”).

I agree with this in general. Most people hide behind “You don’t know how hard and demanding my work is” as they surf Facebook half the day, and similarly most people have no idea how to back-time a project. This is largely because work is often a series of meetings and calls with no clear action items until six days after a meeting you totally already forgot about, and then on the sixth day, your boss throws a heaping pile of turds on your plate and screeches about how it’s an “urgent business need” so you dive head-first into it with absolutely no context around what it is or why it’s important. You hit the deliverables hard for 1.5 business days, then your boss comes to you and says “Oh, that’s not really a priority anymore.”


That’s how most jobs work: it’s a brutally ineffective cycle of hurry up and wait mixed with unclear priorities mixed with people urinating on things to prove they own them mixed with about 80 percent of your co-workers having no time management skills or even taking a second to prepare for the meetings and calls you keep attending with them. And this is how you spend most of your waking hours in the middle of your life! Fun!

Time management skills: How do we improve them?

Here’s the first thing Fast Company says in that article above:

So put yourself in a coaching mind-set. As your employee approaches a long-term project, “Have them make a plan, and then you’ve got to review the plan,” says Tulgan. Include lots of intermediate benchmarks with deliverables and dates. Have the person create a list of concrete actions necessary to achieve each benchmark with estimated time budgets for each task. “Make sure the time budgets are realistic,” says Tulgan. Has he thought about what he’ll need from other departments? Has he thought about what might go wrong? If you arrive at an estimate of four hours for a step, then you can look at his calendar together and block in when that can happen.

This made me want to self-immolate, because it’s the worst “how a manager should act” paragraph I’ve read in a few weeks. What’s described above is micromanaging, plain and simple. When I read the paragraph, I envisioned a parent sitting with a five year-old helping with homework. That’s not what a boss-employee relationship should be like. Everyone in that latter relationship is an adult. Let’s treat them like adults, yes?

Now, that said, I also admitted above that most people have shitty time management skills. So how can we treat people like adults but also boost their time management skills?

Time management skills: The check-in

The next sentence in the FastCo article after that terrible paragraph above leads with: “then check-in frequently.” Bam, there’s your semi-answer. You could have deleted that entire paragraph above and done better with one sentence.

More Articles On Time Management

You might like some of the other things I’ve written on this topic:

Here’s the deal: most managers are not very good at their jobs, and most have a documented hard time setting their own priorities. They tend to rush, hair ablaze, from meeting to call to meeting to call to stand-up to meeting to call (“… and a Partridge in a pear tree…”). What’s lost in everything is the organic check-in with employees to see how things are going. Because you often remove that organic check-in, something happens with a project — a missed deadline, for example — and instantly the manager yelps and bellows about “a sense of accountability” or something. What if the manager had been checking in with the employee throughout instead of racing through their own deliverables? What if there had been some process of organic feedback? Then maybe there would be more context, more time management skills, and we’d understand what happened with the initial deadline.

The cycle should go like this: Project with context provided — > Frequent check-ins — > Project delivered — > Tweaks and iterations.

Instead, this is how it often goes: Project thrown at someone — > Never mentioned or discussed again — > E-mail sent on due date inquiring as to where it is — > Anything short of perfection gets a mini-lecture from manager about “the value of hard work.”

It’s nearly impossible to develop good time management skills in the second set-up, because everything is hair-on-fire, urgent, now now now, and no true sense of context or relevance back to organizational goals.

Let me give you another quick story here. That Fast Company article I’m linking in this post talks about how “one key reason people miss deadlines” — poor time management skills! — is because they’re a perfectionist and don’t want to send subpar work out the door. Hm. That might apply to some people, yes. In reality, that’s largely bullshit. Here’s the reason people miss deadlines: they have no idea what the hell the project even really is, and/or it doesn’t seem to matter to anyone else, so you forget about it too.

After I got canned from my last gig (my first firing!), I heard from a former co-worker that there was a rub on me that I had missed a specific deadline. I went back and thought about the process therein. What had actually happened was that my boss, her boss, and two other people needed to evaluate this project were going to Italy for 11 days for a work deal, and I knew they weren’t going to evaluate it while there. So, I updated everyone on progress and asked to submit when they were back and could consider it. Everyone agreed. Weeks later, that story became a “missed deadline.” Now, would that be poor time management skills? Some might say yes. Personally, I’d say it’s a set of time management skills taking context (people being gone) into account and hoping to deliver a stronger product when they have the time to evaluate it. But for many people and hundreds of managers, all that matters is hitting your mark — which in this case means deadlines. I call this “the due date manager.”

Phrased in more general terms: let’s say your friend mentions something fairly banal to you once, then doesn’t mention it again. You’ll probably forget about it, yea? Then 2-3 weeks later, your friend rushes up to you screaming about that thing. You’re like “Huh? What? Oh, that thing? We haven’t discussed that in weeks…” Your friend is livid, though! He wants answers!

You’d probably think that was a pretty strange situation with your friend, right? I would.

The thing is, that happens between managers and employees every hour in some organizations — and we wonder why time management skills are considered hard to develop. Time management skills come from an intersection of personal aptitude, priority-setting, clarity about role and goals, and feedback and check-ins. They don’t come from screeching and throwing items arbitrarily on a calendar. Managers need to understand that.

Embrace the check-in. Embrace context. That’s where you’ll see time management skills grow.

Ted Bauer

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