Coaching Leaders During Covid

It’s 2022. Strange as it is to write this, that means we’ve been living in a Covid-19 world for two years. For many of us that has meant a shift into remote work and remote leadership. Looking back on these past two years of fully remote leadership, I’ve observed that the stress of Covid-19 has only exacerbated the struggles that many new leaders go through. With that in mind, here are four struggles new leaders commonly face, and coaching lines I tend to employ for each.

Please note, as in all things I try to be empathetic and kind. I myself struggled greatly with these concepts as I transitioned into leadership, and I try and share personal anecdotes and my own struggles with the folks whom I support. Open your heart a little, it helps.


Delivering Difficult News

Here’s the scenario:

A leader is having difficulty delivering difficult/negative news to a team.

Here’s the pitch:

By “protecting” your team from bad news, you create a culture of fear.

Here’s the deal:

Early in my career, I thought that I was being a good leader by protecting my teams. I was causing them harm, but I didn’t realize it at the time. I thought I was being a good leader if I only gave a team the “good news”, the positive outlook, the cheery optimism of having the “best projects in the company.” I thought I was giving them the proverbial “good jobs.”

What I was really doing was building an environment of existential fear. How? By protecting these teams from the reality of the business and attempting to ‘smooth over’ company losses or poor results, I had eroded trust. Visibility, and real honesty drive trust within a team. In removing that, I had affected their psychological safety. They were always waiting for the other shoe to drop. Transparency, accountability, and revenue measurement are a form of kindness to a team. Trust isn’t just built on good news, as we’ll discuss in Assignment of Undesired Tasks below.

Loss of Peer Relationships

Here’s the scenario(s) (this line of coaching is fairly universal):

  1. A newly promoted leader is struggling with the loss of peer relationships on their team.
  2. A newly remote leader is struggling with building team culture over the internet.
  3. A leader is struggling to connect with a new team.

Here’s the pitch:

Don’t be yourself, be the leader you want to be. Lead from your fundamentals, not your personality.

Here’s the deal:

First, remind the manager that it’s their skillset that earned them this role, and it’s through that skillset and leadership experience that they can best help a team. Not personality. Not popularity.

I have found that a bold, clear statement of purpose helps to clear up any misconceptions. To wit, I recommend to all managers: Don’t be yourself! Be the leader you want to be. Lead from your fundamentals, not your personality.

Jokes and interpersonal ribbing can ease tension, but possibly at the expense of someone’s emotional safety. There’s always an imbalance of power between a leader and those they support. Friendships are not built on power imbalances, and businesses do not run on friendships. All of the benefits of friendship in a business context flow upwards towards the business, and away from the individuals you support. “Oh, can you stay a few hours extra to help out buddy?” “I know you have family commitments, buuuut can you come in early for a meeting just on Mondays? To support your work family??”

Lead through your fundamentals. This is a kindness to those you support.

  1. Build a culture of excellence and pair it with empathy.
  2. Set an expectation of mentorship and growth mindsets.
  3. Value accountability at all levels, have clear measures of success, share outcomes widely.
  4. Listen. If you find yourself interrupting folks, sip a drink during 1:1 meetings.

Assignment of Undesired Tasks

Here’s the scenario:

A leader is struggling with the assignment of undesirable tasks

Here’s the pitch:

Trust isn’t built by throwing goodwill over a wall, it’s a relationship you build together collaboratively.

Here’s the deal:

There’s this concept folks like to talk about in team leadership, that of the “trust jar”. It goes like this, every time you do something that builds trust with a team, you’re “putting a quarter into the trust jar.” It’s a nice visual metaphor of the trust you build with a team over time.

The thing is, that’s only half the story. If you never have to ask for trust, if you never ask a team to suspend their disbelief and (in this case) do this undesirable task, then you’ve not built real trust. You’ve just banked goodwill. You’ve turned your trust jar into a wishing well, when it should really be more like the ‘take a penny leave a penny’ tray at the store. A shared trust, going both ways, building depth and value together. It is through this transparency and the shared shouldering of burdens that you truly build trust with your team.

Meeting Team Commitments while Growing a Team

Here’s the scenario:

A leader is struggling with team growth while still meeting team commitments

Here’s the pitch:

Every problem is an opportunity that someone needs, be an opportunity leader and pair them.

Here’s the deal:

A business is really just a collection of problems. At all levels and at all times we’re facing challenges, prioritizing which ones to tackle and how to do so. An infinite mountain of problems, and we ski down the top slope of it every day. How then, to think about team growth when there are nothing but problems to face?

Remind those that you support of the mission. Of your responsibility as leaders to help others. Always tie it back to the mission, and to an empathetic outcome. Every problem that your business faces is really just an opportunity that someone in your organization needs. Maybe it’s the opportunity to learn a new skill. Maybe it’s the opportunity to help just one more person. Find that silver lining. Find the person who this challenge is also an opportunity for. As leaders we’re constantly measuring, learning, attempting to become better at what we do and in helping those we support. You should know (and if you don’t, well then get to knowing!) what areas your folks are looking to grow in. It’s a regular topic at your weekly check-ins, and you never want someone you support to be in the dark about their own performance and growth. Pour yourself a nice slow-sippin drink, and get to listening.

Here’s a technique that I often employ with new leaders. I ask them if they know about the two purposes for every meeting. That usually piques their interest, and we dive in. The first purpose is obvious, it’s the stated purpose of the meeting. Every meeting has an outcome, decision or artifact that is clearly stated and obvious to all involved. If not, cancel that meeting as it’s an email in disguise.

The second purpose for every meeting is in opportunity leadership. Be on the lookout for problems that are really opportunities for folks you support (not just folks on your team, a good leader supports all departments.) You’d be surprised how quickly after finding out about a skill or growth area for an individual that an opportunity will present itself. Teaching this, truly embedding a growth mindset within your teams will pay off dividends for many generations of leadership. Encourage folks to talk about it plainly and transparently.