Manage your people with care

Banner image of manager with direct reports
Summary
In an async-first culture, the manager is one of the bridges for the employee to the organisation. To show that the company cares, managers should care as well. This post describes some ideas to show that care.
  1. Aim for a 1:5 ratio or less between managers and direct reports. That way managers will have time to spend with their people without oversubscribing themselves.
  2. Run effective 1:1 meetings. Make these about building relationships, sharing guidance and offering help. Avoid transactional discussions here.
  3. Share timely, atomic feedback. The radical candour framework is an effective way to do this.
  4. Be there for your people when they need you, even if it's unscheduled. This'll help address the unpredictable situations that can come up at work.

In the tech industry the word “manager” is rather unpopular. Companies go to extreme lengths to say they’re “flat” or that they have “no managers”. If they have managers, they go to extreme lengths to hide this behind many euphemisms - “performance partners”, “success catalysts” and whatnot. This doesn’t lead to good leadership. The state of denial causes confusion. Since the company doesn’t acknowledge that they have bosses, there’s no obligation on anyone to be a good boss. At scale, the complete model breaks down, because employees don’t have anyone to talk to who shows a personal interest in them, their work and their careers.

I think our industry has over-corrected for the phenomenon of poor managers, a.k.a “bosses”. Instead of training people to be good bosses, we’ve propagated the myth of flatness. Anyone who’s worked in a largish company knows that beyond a certain point there’s always a hierarchy. I wish companies fessed up to it instead of tip-toeing around this obvious reality. It’s ok. The world will not descend into a black hole if we accept that our “flat culture” has managers. We won’t become a worse place to work overnight if we use that word. It’ll just make responsibilities clearer.

In an async-first culture, the role of a manager is crucial. If the company is the mother-ship, the manager’s the employee’s bridge to it. They should be the individuals that know the most about their people, their skills, abilities and strengths, their personalities and their aspirations. You need managers who lead with care. In today’s post, I want to address how you can show that care as a leader and a manager. Let’s get right into it.

Don’t oversubscribe yourself

First things first revisit the people management relationships in your sphere of influence. It’s really tough to manage over 4-5 people with care. In many companies, the quest for flatness leaves the only official managers in the system with dozens of direct reports. You need to mend this first.

Work with your HR team to establish meaningful reporting relationships between people. This doesn’t have to translate into a complex management structure for work. The idea is to find each individual, a people manager who’s close to their work. For example, a tech lead can manage the developers on their team. An engineering manager can work with the tech leads. So on and so forth. 

The rule of thumb is to get to a ratio of about 1:5 between managers and their direct reports. Why 1:5? Well, if you’re managing people then you need to spend 1:1 time with them. One hour a day will mean you can meet everyone individually each week. If you can’t get to this kind of ratio, you’ll always be behind the eight ball. 

  1. You’ll make compromises in terms of how much time you spend each week with people;

  2. or you’ll stretch yourself and spend a lot of time in meetings with very little time for work.

 And #2 doesn’t work. As Kim Scott says, you need to keep the “dirt under your fingernails”.   

Image of manager with direct reports

“In order to be a good partner to the people on your team, and in order to keep the GSD (getting stuff done) wheel spinning efficiently, you need to stay connected to the actual work that is being done—not just by observing others executing but by executing yourself.”

Meet people 1:1 

Which brings me to my favourite people management activity. One-on-one or 1:1 meetings. In my profession, I alternate between individual contributor and people management roles. My preference is to set aside an hour each week to talk to each of my direct reports. Over the years, I’ve developed a system for these meetings. Between my direct report and myself, I maintain a shared document, which has a running list of topics that need the other person’s attention. The cool thing is that we resolve many of these topics well before the 1:1 by dropping notes in the document itself. Which then leaves the meeting open for non-transactional conversations. 

 Despite being an introvert, I surprise myself with how much I can talk at these meetings. In fact, that’s an anti-pattern. This meeting is for the direct report - give them the space to direct the meeting and take as much airtime as they need. There’s always heaps to talk about. Here are some topics I cover in my meetings.

  • Personal well being. I like to know how people are doing, not just at work, but also (if they’re comfortable sharing), in their personal lives. I try to be human as well and share what I’m up to. There’s nothing special about me as a reporting manager. I just have a few more years or work experience or maybe a little more tenure in the organisation. The more my colleagues see that, the more open they can be with me. 

  • Sensitive conversations. Some sensitive conversations can’t happen on the shared document. For example, my colleagues may want to talk to me about interpersonal challenges at work. I prefer to handle these conversations in a real time conversation.

  • Progress on expectations. The reporting relationship usually corresponds with a performance management process. 1:1s provide a predictable time for both of us to agree on how much progress my direct report has made on their expectations. We don’t have to do this each week, but having the space to do it is important, and it gives us room to course correct if we have to. I also use this opportunity to evaluate their workload. People’s time is a zero-sum game. If a new piece of work comes in, something else has to go out. Understanding people’s skills, their interests and their capacity helps me work with them to keep them in the Goldilocks zone.

  • Helping each other. Reporting relationships aside, we’re colleagues. I’m quite candid to ask for help, though I don’t always wait for the 1:1 to do this. Since the 1:1 is open-ended, I can find out ways to help the other person. Managers need to understand the work their people do. That’s when you can roll up your sleeves and offer meaningful help. Advice is cheap, execution is costly. By helping, you share some of that execution burden and build a strong relationship between you and your people.

  • Feedback. In an ideal world, I wouldn’t wait for a 1:1 meeting to share feedback. I enjoy sharing feedback in the work's context or the incident I’m giving feedback for. That way people have the chance to act on the feedback and the specifics are fresh in their minds as well. If the trust level between me and my direct report is high, I’ll often share feedback asynchronously as well - especially feedback to strengthen their confidence. However, if I'm trying to improve their effectiveness through feedback and we’re still developing our relationship, I prefer waiting for a synchronous opportunity to talk. Sometimes the 1:1 is the earliest available synchronous opportunity.

Demonstrate radical candour

At the start of my agile career, I was very lucky to work with Patrick Kua. Amongst other things, Pat taught me about feedback; that there’s no such thing as “negative feedback”. Feedback, Pat said, had only two purposes.

  1. Strengthen confidence - i.e. tell the other person what they’re doing well that they should continue doing.

  2. Improve effectiveness - i.e. point out what the other person could change so they get better at what they’re doing.  

Each of these purposes comes from a place of empathy and positivity, so Pat argued that all feedback is positive. And if in your mind, the feedback is for some other reason, then think again. It’s probably not feedback. 

Over the years, I read books like Crucial confrontations which talked about addressing feedback conversations with safety. Between what Pat taught me and all of my other reading, I’ve found the book “Radical Candor”, by Kim Scott to be the best summary of an effective feedback approach. As the above diagram shows, you display radical candour when you care personally about the people you manage and when you can challenge them directly about their work.

Radical candour exists at the intersection of caring personally and challenging directly.

While I suggest you read the book to understand the approach in its entirety, here’s a summary. 

  • To show care, you need to build trust. This takes time. When you share feedback about certain incidents, you can show care by acknowledging the other person’s positive intent. You can create safety by asking them for their perspective.

  • To challenge directly you can follow the situation, behaviour, impact framework: 

    • the situation you observed;

    • the individual’s behaviour in that situation;

    • and the impact of that behaviour.

For example, “Ravi, when we were in the sprint review meeting and I asked you to make a note of the client’s feedback, you didn’t acknowledge me or add the item to the meeting notes. This made me feel like you were ignoring me. We also haven’t logged an important fix that the client wants.”

Kim also describes anti-patterns to radical candour, which you should avoid.

  • Obnoxious aggression. Challenging directly without showing personal care.

  • Ruinous empathy. Showing care without challenging directly.

  • Manipulative insincerity. Neither caring, nor challenging directly.

As a manager, you need to be adept at this framework of building relationships and sharing feedback. It’s best to share feedback in a timely and atomic fashion. When you let feedback pile on for too long, you’ll construct stories about the other person in your head and it’ll ruin your working relationship with them. And yes, the best way to build a culture of radical candour is to first solicit feedback. In Kim Scott’s words, it “proves you can take it before you dish it out”.


If I could end this post with a piece of parting advice, I’d say - be there for your people. Sometimes your direct reports just need an unscheduled chat, or a phone call. There could be many reasons for this - a stressful situation at work, an interpersonal blow up or just someone facing a tough time. There needs to be enough time on your schedule so you can address the unpredictable. All the more reason to make meetings the last resort

 This post ends my series on leadership. If you remember, we started this series as a detour, so I could figure out content for my book. I feel like I’ve covered a lot of ground since then. If you’ve been reading the posts since, thanks for following along. It’s now time for another section! 

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