Summary

Bosses don’t often receive training to be effective people managers. This lack of awareness and people management skill can often lead to disgruntled employees who’re at flight risk. The boss’s boss; i.e the super manager, can preempt dire people issues, by implementing practices that help them listen directly from their employees. In this post, I discuss three such techniques.

1. Skip-level meetings

2. Office-hours

3. 360 reviews

This isn’t an exhaustive list of ideas, but a suite of the most essential practices. You can be as creative as you like!

Are you a super manager, i.e. a manager of managers? In that case, I have a story for you. A friend recently quit their job. His new job, however, wasn’t much better. The pay was roughly the same as his current job, though he’d have more opportunities to ply his core skills. So when we asked this friend why he was switching, he had a one-word response for us - “Manager”. He then repeated the now-familiar maxim, 

“People don’t leave companies; they leave their managers.”

His response surprised me. When I probed further, my friend—let’s call him Bobby—said his boss made him feel “all of six inches tall”. 

• The boss took none of Bobby’s experience into account. Bobby felt no better than a fresher straight out of college. In every other conversation, the manager would talk down to my friend and patronise him as if this were his first rodeo.

• Bobby’s values and work style differed from their manager’s. Bobby cares about deep work, and the manager is a hustler. Autonomy, mastery, and purpose are secondary concerns for the manager, but Bobby cares deeply about them. “There was never a moment for reflection when working with this manager,” said Bobby.

• In the last few months, Bobby said he was unlearning what he thought were his most vital skills and putting on a charade of performative productivity only to please his boss. He felt terrible about this.

All this said, Bobby didn’t think these were intractable problems. “They’re nice,” he acknowledged, “but they didn’t try to learn how to get the best out of me”. It seemed like this boss didn’t even exploit the weekly one-on-one meetings to get to know Bobby well. They wouldn’t even pay attention to the agenda Bobby would throw up for these meetings or the documents Bobby would write up to set context for topics that mattered to him. Of course, there were superficial pleasantries and the customary, “How’re you doing?” but after that, the meeting would veer into task reviews and status updates. “The working relationship had become a one-way street. I’d do all the work, and they’d do nothing for me in return.”, said Bobby. 

If I were to tell you which company Bobby worked for, you’d immediately recognise it as a people-centric company. In fact, Bobby’s super manager is a LinkedIn guru who writes about topics such as “people care”. How’d such a dire situation get past the super boss? Bobby’s my friend, and I’m biased, of course, but now that he’s quit, I’m sure the company will struggle to find an equally talented replacement. It’s a loss for the company, and it may have been easy to avoid if the super manager had their ear to the ground.

Tech is a fast-moving industry. Many employees become people managers with no training on how to care for the people under their wing. While that’s the status quo, the system needs checks and balances to avoid a Bobby-like situation. If the manager fails, the super manager should be able to detect and address the problem before it gets out of control. It’s not rocket science, but it won’t happen automagically either. So, in the rest of this post, I want to share three ideas for you, the super manager, to keep your ears to the ground so you can help your direct reports manage people better.

Skip-level meetings

If an employee feels stressed, they often also feel unsafe. It isn’t easy for them to reach out to a super-boss to tell them how they’re feeling, however well-intentioned that super-boss may be. Hierarchies are a natural reality of corporations, and it’s not unreasonable for stressed employees to believe that there’s a clique between their manager and the super manager. All this creates a power imbalance that makes it hard for employees to approach their boss’s boss. How do you gather the courage to tell your super manager that their direct report may be mismanaging you? It’s hard!

Skip-level meetings make this easy. It’s where super managers proactively meet with their direct report’s direct reports. In many companies, the big bosses conduct these meetings in small groups. In other, more intimate setups, super managers make it a point to meet people one-on-one at least once a quarter. You can adapt this practice to how much time you have on hand and people’s safety levels.

In my experience, the first few meetings yield little insight. Most people still don’t know if they can trust you. Don’t let people’s reluctance to be candid discourage you. Give it time and build trust. The idea is to show up each time on a promised schedule. Consistency will drive the honesty you’re after. Eventually, people will open up as they feel safe in that setting. And when they do, be a truth seeker. Your direct report may well be your back-slapping buddy outside work. But don’t let that relationship cloud your judgment. Take all feedback on board. There should be no consequences for speaking up. Reflect on the feedback and use it to coach your direct report to be a more effective people manager. 

Office hours

We’ve discussed how “office hours” can help soloists protect their deep work capacity on this site. 

“The idea is simple. Institute a recurring time when a particular soloist is always available to help anyone who needs their time. They’ll be in their “office”,. E.g. from 1500 to 1630 IST, on Mondays, Wednesdays and Thursdays, the product manager is available to answer questions or problem-solve with anyone who needs their time.”

Guess what? You, the super manager, can adopt the same idea. You’re a soloist, too, aren’t you? Think of this as an “open-door policy”. Anyone can walk through your virtual door to seek you out and share what’s on their mind. You tell them when and where that door will be. 

If an open-door policy was necessary at the office, it’s even more critical in a remote setting, where people don’t see you, and there are no visual signals to tell them you’re available for a chat. A recurring meeting on the team calendar, accompanied by a persistent Zoom link with a waiting room enabled, provides that visual signal.

Yet again, you can decide the frequency of these office hours. You could get away with once a fortnight if you know your direct reports and ace people managers. But once or twice a week can be a good starting point. Ask yourself how often you would keep your doors open if you were in the office.

360 reviews

And finally, something a bit more conventional. If you have a large team of direct reports and they have up to six direct reports each, the numbers can add up fast. You need a more scalable and structured way to gather feedback. 360 feedback surveys allow you to collect anonymous feedback from your direct reports’ teams every few months. They’re easy to synthesise, particularly with AI, and you can slice and feedback across many parameters. 

Like anything else as powerful, though, there are a few pitfalls to be aware of with 360 reviews. First, if you run such surveys, commit to following up. No one enjoys shouting into a void, and if people don’t see any impact of their 360 feedback, you’ll induce feedback fatigue. Once people give up, you’ll also lose credibility as a leader.

Second, 360-degree surveys are rather impersonal. They can complement, not replace, more intimate interactions like skip-level meetings and office hours. If you can’t conduct a quarterly skip-level meeting, you could alternate these meetings with 360-feedback. Whatever you do, don’t discount the value of a real-time conversation. I say this even as the author of “The Async-First Playbook”.

No listicle of this nature is ever exhaustive, and the three ideas in this post are not the end-all either. If you have the time and interest, you can try other techniques, such as facilitating retrospectives for different teams or shadowing your direct reports during team interactions. You can institute reverse mentorship spaces where people with unique skills and knowledge can teach their managers a few tricks. Management hackathons can help you work with teams and their managers to improve a specific way of working. Activities like these can level the playing field between bosses and their teams and create an egalitarian organisational environment.

But time is often a scarce commodity. If that’s the case for you, the three practices I shared represent the most conventional fail-safes you must implement. Most tech firms self-certify themselves as “people-centric”, but actions speak louder than words. How you, the super manager, keep your ears to the ground is part of those actions!