The fundamental soft skills (but not the *most* obvious ones)
I started writing this newsletter because there are soft skills that nobody teaches you, and that will quickly become the limiting step on your career advancement. Technical skills and subject matter expertise get most of the glory when it comes to career advancement, but soft skills are immensely important — and it can be hard to figure out on your own if they’re holding you back, because people won’t always tell you.
It occurred to me recently that I jumped right into really specific things, and most of the skills I’ve talked about in Diamond Pencils have some sort of managerial component. They’re about getting what you want from other teams, or from your teams, or about managing projects, or becoming a manager.
And that makes sense because those are goals for a lot of people. But it also undersells the importance of a few very important skills that are about how you individually work.
So this is about the fundamental soft skills. Not the super duper eye-rolling obvious ones like “show up to meetings on time” or “make sure you hit your deadlines,” and I’ve also left off variations of “don’t be an ass.” Instead, these are the things that every person working in a team environment should keep in mind.
They are, in a few words:
Not just hitting deadlines. Setting deadlines, even when you aren’t asked to.
Communicating about timelines even when they are on track
Prioritizing the highest impact work and actively managing your manager to do so
Managing your own schedule
When to push for a decision in a room of people with equal rank
Extracting every bit of value from time with your manager
As you go through the list, you’ll notice a couple of themes: becoming increasingly autonomous in your own work and making sure no one ever wonders “hm, I wonder what they’re working on.”
1. Hitting a deadline, sure. But really it’s setting your own deadlines even when you aren’t asked to.
Though it may defy logic, the easiest way to screw up a project is to give it too much time — enough time for people to rethink, revise, have second thoughts, invite others into the project, get more opinions, conduct tests… – Ken Segall, Insanely Simple
Yes, you want to hit deadlines when they are handed to you by your manager. And I don’t want to undersell this, because there are definitely smart, talented, hardworking people who struggle with deadline management, and consistently moving deadlines will hold back your career.
But there’s a level beyond just hitting the deadlines you’re asked for, and that’s actively assigning yourself deadlines for tasks as they arise (assigned or not).
See the difference in these two conversations:
Manager: Hey, I have this report I’d like you to work on. It’s not incredibly urgent, but it is important that it gets done. You: Yup sounds good, I’ll get on it!
Manager: Hey, I have this report I’d like you to work on. It’s not incredibly urgent, but it is important that it gets done. You: Hm, ok yeah — based on the scope I think I can have that over to you by next Thursday, but let me get started and send you an update on the timeline by EOD Tuesday.
Yes, the manager can set deadlines themselves, or specifically ask you to set a deadline. But most of the time — at least for knowledge workers — managers are not primarily managing a production workflow (e.g. X units of work in Y amount of time) and are instead managing projects intended to create an outcome.
And this is a pretty big shift for a lot of people when they come into knowledge work environments, because it’s not true of many of the very first jobs people are likely to have (where the manager sets what gets done) and it’s not true of school (where homework is assigned and has due dates).
In those two scenarios above, which one inspires more confidence in you that the report will get done in a timely fashion? And even though the conversations are just about deadlines, don’t you also get the sense that the second scenario will have the higher quality report?
Setting your own deadlines is part of communicating timelines (the next bullet). But it also makes people more confident in your work, and is actively good for you — you always want people to have a sense of what you’re working on (“Hm, I don’t really know how they spend their time,” is not a good sign for a career), and setting deadlines like this makes it less likely that you’ll get buried under tasks.
2. Communicating actively about timelines when they change, but even when they are on track.
I felt I could turn things around, but I needed to buy time. I did it, in part, by keeping Eddie Jr. in the loop; fully informed—perhaps overly informed—on every single phase of the operation. This included providing him with a budget manual (thick), an operations manual (thick), a personnel manual (thick), an overall set of job descriptions that included the specific job of each player and my evaluation of that individual (thick), and a detailed listing of my performance goals and expectations (even thicker).
On and on and on. Paper. Paper. Paper. The information was not frivolous "filler," but substantive and sizable. I wanted the owner (and his advisers) to understand that I was applying maximum effort and paying attention to every single solitary detail of the family's massive financial investment. I believe the voluminous detailing of my efforts and plans bought me previous time. – Bill Walsh, The Score Takes Care of Itself
I love this quote from Bill Walsh because it lets me harp on a point I have already mentioned twice: you always want people to know what you are working on.
Here’s a benchmark I use for myself: if my boss has to ask for a status update on a project, I have undercommunicated the status of that project.
Why? Because your boss asking you for a status update isn’t the first time they’ve thought about the status of the project. They’ve probably wondered loosely about how the project is going, or if it’s on time, and then checked the deadline and thought something like “well it’s still a bit from the deadline, and I should trust the team to get it done when they said they would” and then decided against checking in. And then the next day or week something happens or they just change their mind, and finally ask.
Phew! Even writing that was a little exhausting. You don’t want to put your boss in a position to wonder what’s going on with your project. When they think “what’s going on with that project” their immediate next thought should be “oh yeah, I just got an update about that this morning,” and then they can go and read your update.
Some notes:
Communicate the timeline of things even when they are on time. First of all, this raises the confidence level in your work. Second, if a deadline does wind up slipping, you won’t have to deal with questions like “has this been behind schedule the whole time and no one told me?” Third, you can give timeline updates along with status updates, and your boss may want to review some piece of work at an earlier stage — which could avoid major rework down the line.
You can’t rely on your boss to check anything. As I’ve written in the past, your boss is an idiot, and so am I. I don’t care what kind of project tracker you use. It’s useless, at least in this context. Your boss manages multiple projects and they all have tracking; when they are on a call with their boss, they need to be able to answer questions without digging through your project management tool for the answer. Your updates need to be sent as easily digestible text in some form of direct message.
Tailor your update frequency to the pace/urgency of the project. At the end of Q3 we discovered a change in definitions led to a change in a number we report quarterly. This was technical enough that we needed to get our data team involved — but every day we didn’t have the number I slacked my boss a status update of our progress to that point.
Make sure people know the status of what you’re working on.
3. Prioritizing the highest impact work (and shipping work), and actively managing your manager to that end.
Knowledge of principles also lets you weigh one method against another realistically, and include methods with a long tradition of use. – Karen Pryor
You should always have more to do than you can accomplish on a given day.
Notice I didn’t say you will always have more to do (although that is often also true), but that you should have more to do. This is actually a desirable state of affairs.
Strategy isn’t just about what you do; it’s about the good ideas you choose not to pursue. Having a lot to do is good because it forces prioritization, and if the person exists who is so perfect a prioritizer that only 100% important to-dos wind up on their to-do list every day, I have yet to meet them.
Ok, so having a lot to do is an exercise in prioritization. This soft skill isn’t about how to prioritize, but about what prioritizing means:
You have to prioritize the highest impact work, and that means setting aside your other to-dos. This is not obvious, and I’ve made this mistake as a manager on several occasions. Often that moment looks like “wait, they’re spending their time on what?!” When there’s very important stuff to get done, it’s ok and even expected (and desirable!) that other stuff takes the back seat.
Shipped work exists. Partially completed work does not. I would rather be at 100% completion of one project than 80% completion of three projects. Until work ships, it has no value to the organization. So your prioritization should prioritize the most impactful work, and it should prioritize shipping work that is complete vs. making incremental progress on many projects at once.
You’ve gotta work with your manager on prioritization. You have finite hours in the day and both you and your manager want them going to the most important work. As with the previous skills, actively communicate that you are working on prioritization, and enlist your manager’s help. This is what will let you set aside your other to-dos, and will keep a manageable amount of work on your plate. You want enough work so that it forces prioritization, not so much that you burn out!
The first bullet is the most often missed. People have a tendency to just stack new work on top of old work and then get stressed that they’re not finishing anything. Forget that! Drop everything (or, you know, a lot. The amount you can.) and ship the most important stuff.
4. Your own schedule management. What you work on, but also how you batch work.
There are two types of schedule, which I'll call the manager's schedule and the maker's schedule. The manager's schedule is for bosses. It's embodied in the traditional appointment book, with each day cut into one hour intervals. You can block off several hours for a single task if you need to, but by default you change what you're doing every hour.
When you use time that way, it's merely a practical problem to meet with someone. Find an open slot in your schedule, book them, and you're done.
Most powerful people are on the manager's schedule. It's the schedule of command. But there's another way of using time that's common among people who make things, like programmers and writers. They generally prefer to use time in units of half a day at least. You can't write or program well in units of an hour. That's barely enough time to get started. – Paul Graham, Maker’s Schedule, Manager’s Schedule
I actually think I covered this point reasonably well in my second post — Break big things into small t.h.i.n.g.s. In that piece, I talked about the productivity system I used in college and how it translated to the working world.
The big lesson here is that managing your own schedule means breaking your tasks down into more specific chunks than most people break them into. I won’t belabor the point; you can go read that post.
The other point to bring up here is that you’ll want to balance your deliberate tasks and your interruptive ones. It’s just not possible to do good, deep work while responding to a bunch of emails or getting messages on Slack. Most people find a balance of this for themselves, but it’s worth pointing out — batch your admin tasks, focus your big projects on the hours of the day you have the most energy, and break things into chunks to execute them faster.
5. Decisiveness (especially in a room of equals), pushing for a decision when it’s clear you’ve reached saturation.
It is legitimate—in fact, sometimes unavoidable—for the senior person to wield position-power authority if the clear decision stage is reached and no consensus has developed. It is not legitimate—in fact, it is destructive—for him to wield that authority any earlier.
– Andy Grove, High Output Management
I’ve been in a lot of meetings (less as time has gone on) that started out as 20 minutes of really great discussion and then ended with 40 minutes of doing that same discussion two more times.
As Andy Grove points out in High Output Management, this is common in rooms of people of the same hierarchical position. No one wants to stick their neck out, or no one feels like they have the authority to tell other people that it’s time to move on to next steps, and so the group continues to rehash the same info and doesn’t actually arrive at next steps or a plan of action.
If you notice that this is happening, you have an opportunity to make an important contribution! You don’t have to decide the next steps, you don’t have to tell anyone what to do, you don’t really have to stick your neck out at all — all you have to say is “I think we have enough info to start making some decisions about next steps.”
There’s an idea in qualitative research called “saturation.” When you do qualitative research, one of the hard questions to answer up front is “how many people do I need to interview.” Depending on your topic and your audience, you won’t necessarily be able to answer this right away. But you can tell you’re done when you reach “data saturation” — you start hearing the same ideas from each new participant.
Here’s a reasonable definition from the top of Google:
“Saturation in qualitative research is when, through the course of interviewing (or observation), you notice the same themes coming out, repeatedly. As you interview more and more participants, you stop finding new themes, ideas, opinions, or patterns.”
Meetings and decisions can also reach saturation, and that’s the time for you to pipe up and say “hey knock it off! We’re saturated! We’ve got to move on!”
I think this skill is slightly less fundamental than the others in that you can get by without it, but if you want to advance in your career it will absolutely be necessary — you need to be able to get a meeting to agree on next steps.
6. Extracting every bit of value from time with your manager
Effective leaders ask questions rather than providing answers. The questions are key. Great leaders don’t tell people, they don’t direct people, and they don’t order people around. They facilitate great thinking through self-reflection. – Cy Wakeman, No Ego
Early in my career I would sidle into my one-on-one with my manager all cool like and go “hey. what’s up” (all lowercase). We’d talk generally about how I was doing, and because I was generally doing ok we didn’t have that much to talk about.
That was a mistake.
Now my bosses have been on the receiving end of some truly prodigious one-on-one agendas. I mean really, I’m pretty sure I’ve put together 1,000 words worth of agenda on multiple occasions. Agendas are structured with a section heading and bullets, but the bullets are full sentences and paragraphs — way more detail than “let’s talk about sponsorships,” or similar — because I want my manager to have most of the context to start thinking about the subject before we ever get on a call.
Your one-on-one is your time. Your boss is there to help, and they should not be setting the agenda in most cases — not the least because they probably do a lot of one-on-ones (every direct report, skip-level meetings, peers, their own boss), and they don’t need more admin.
But beyond taking load off your boss, this is your time to solve all (ok, most of) your problems. You can use this time to get feedback on work, you can give more detailed status updates, you can ask big-picture questions about prioritization of your work or get thoughts on how to approach next steps. You can ask how your boss is feeling about…whatever! The company, the team, the project.
There is a lot of value you can get out of these conversations, and if you spend 10-20 minutes prepping the meeting you could get many times that impact back. At a minimum, I keep a notepad that I update with things to talk about throughout the week, so I always have a list and never have to wonder “hm what’ll we say?”
Is every meeting agenda 1,000 words? No! Of course not! There are even weeks we end early. But by and large I don’t struggle to fill time in my one-on-ones with my boss, and neither should you. I think of the skills on this list, owning your time with your boss is the most overlooked — and it can only help you develop each of the others.