Lead with Support Catherine Insler Lead with Support Catherine Insler

Everyone got the invitation

You invited every supervisor. Three signed up. Before you decide who wants to grow, find out what the others needed to arrange just to be there.

A woodland path crossed by exposed tree roots, with fallen leaves along its edges.

You send every supervisor an invitation to a development session next Thursday. Anyone interested in taking on more responsibility is welcome.

Three people sign up.

One person you’d hoped to see doesn’t. They’re good with new employees, and you’ve watched other supervisors go to them for help. You think they could do more, but you’re waiting for them to show some interest.

Later, you ask why they didn’t attend.

“I couldn’t get coverage.”

They asked two people. Neither could take over, so they worked their shift.

You hadn’t needed to get involved in coverage for the people who attended. One already had another supervisor on duty. Someone else’s manager rearranged the schedule. By the time they arrived, all of that was settled.

You sent everyone the same invitation. It seemed reasonable to leave the next step to them.

But you’d already started drawing a conclusion about the person who stayed behind.

Field Notes
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You were waiting for initiative

You don’t want to chase people into development. You want them to have some say in where their careers go, and putting their name down seems like a reasonable place to start.

The supervisor who missed the session did take a step. They asked for coverage twice. You didn’t see those conversations. You saw that they weren’t there.

Had you never asked, you might have gone on thinking they weren’t interested.

It’s easy to do. You’re responsible for a lot of people, and attendance gives you something concrete to work with. You know who came, who asked questions and who stayed afterward to talk. You have less information about someone who couldn’t leave their shift.

That gap can find its way into decisions you make later.

Who comes to mind for the next assignment?

When a project needs a lead, you remember a conversation from the session. One supervisor had a useful suggestion. Another described how they’d handled something similar.

You can picture either of them doing the work.

The person who stayed behind hasn’t had that conversation with you. Their name may still come up, but you have more recent examples for the others. Choosing someone you’ve heard from feels well supported.

Meanwhile, the absent supervisor continues training new employees and helping colleagues through problems. You value that work. You may also have become so accustomed to relying on it that you haven’t considered what it takes for them to step away.

A person can be doing work that prepares them for more responsibility and still struggle to get released for the session where you’re looking for that readiness.

Read the schedule alongside the invitation

Before offering the session again, look at what attending required.

Did supervisors need to arrange their own coverage? Could they authorize a schedule change, or did they have to find someone willing to swap? Were their managers expected to make time for development?

You may find that you encouraged attendance without giving anyone responsibility for making it possible.

Then each supervisor had to work out what “you’re welcome to attend” meant on their shift. For one, it meant accepting an invitation. For another, it meant asking favors and hoping the manager approved.

Leaving those arrangements to individuals can feel like giving them ownership. It also means the people with the most help have less to do before they can say yes.

Coverage won’t arrange itself, and someone has to stay behind. If the same dependable person repeatedly covers while colleagues attend, that needs attention too. Their reliability shouldn’t keep costing them their turn.

You might need to agree on coverage before sending the invitation, or run the session again for the people who missed it. Where you can’t make it work yet, be clear about when you’ll revisit it. They shouldn’t have to keep asking whether you meant the offer.

One thing to carry

Think about someone you’ve been waiting to see step forward. Perhaps they’ve passed on several things, and you’ve stopped suggesting their name.

There may be a reason you don’t know. There may also be a condition you have the authority to change.

Before the next invitation, ask what kept them from taking the last one.


Field Notes

Read your own terrain, every Sunday

One leadership signal a week, read through the map, so you know where you're standing and what to do next.

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They’ve already solved the problem

They’ve made the calls, checked the alternatives, and come to you with a specific request. Before you start solving the problem, listen for the part they actually need you to decide.

A wooden garden gate standing slightly open, with a path beyond it.

Someone asks if they can leave an hour early for the next two weeks. Their childcare arrangement has fallen through.

You look at the schedule. It might take a little rearranging, but you think you can make it work.

"What happened?"

They explain. Someone who usually helps isn't available anymore.

"Could someone else pick them up?"

They've tried that.

"What about the after-school program?"

There's a waiting list.

You're working through the problem together. At least, that's how it feels to you. People bring you problems all day, and helping them find a way forward is part of what you do.

But this person came with a specific request. They've already made the calls, checked the alternatives, and worked out an arrangement that would get them through the next two weeks.

They need your answer about the hour.

Now they're walking you through everything they tried before they came to you.

Somewhere in the conversation, the task changed. You're trying to solve their childcare problem. They're trying to find out whether they can leave at three.

Field Notes
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Listen for what they're asking

"I don't know how I'm going to manage pickup. Can you help me think through it?" opens a conversation about possibilities.

"Can I leave an hour early for the next two weeks?" asks you to consider a particular arrangement.

Both involve a problem. Your part in each is different.

In the first conversation, exploring options together may be exactly what the person needs. In the second, they may have done considerable work before approaching you. The question that reaches your desk is the part they cannot decide for themselves.

When you start suggesting alternatives, you can accidentally send them back through work they've already done. Each suggestion requires an explanation. Each explanation brings more of their private life into the conversation.

You may pick up useful context. For them, it can feel like having to prove the request is reasonable in the first place.

Your questions carry the decision

A manager's question has weight because the manager controls what happens next.

"Could your partner do it?" might feel like an ordinary suggestion. To the person waiting for your approval, it can sound like a condition: before I agree, show me why your partner can't.

Now they have to decide how much to say about their relationship, someone else's job, or an arrangement they would rather keep private. They may answer because they trust you. They may answer because they need a yes.

You cannot always tell which.

This is slippery precisely because you're trying to help. You're paying attention, making time, and drawing on experience. Those are things you want to bring to management. But they can carry you beyond the help someone actually requested.

You can leave the conversation feeling that someone opened up to you. They can leave relieved about the schedule and wishing they hadn't needed to explain so much.

Work on the part you're responsible for

A specific request still needs consideration. There may be coverage to arrange, work to hand over, or a limit on what you can approve.

Those questions belong in the conversation.

Which days do they need? What happens during that last hour? Can the team cover it? When will you check whether the arrangement is still needed?

You can be thorough about those things without taking responsibility for reorganizing someone's family.

If the request cannot work as proposed, explain the actual constraint. That gives you something concrete to work through together. If you need more information, be clear about what you need and why.

And when you're unsure which conversation someone wants, you can ask: "Are you looking for help thinking through options, or do you need me to consider this arrangement?"

That small check can save both of you a much longer conversation.

Give the answer first

Sometimes you know early that you can approve the request. Then concern takes over, and you keep asking questions before saying so.

The person across from you is still waiting.

"Yes, we can make that work. Let's sort out the coverage."

Once they have the answer, they can choose whether to tell you more. You can still care about what they're going through, and they can still welcome it.

But they no longer have to wonder whether the next detail is the one that will get their request approved.

One thing to carry

The next time someone brings you a problem, listen for the work they've already done.

They may need your ideas. They may need you to make a decision. They may have reached the one part of the solution that requires your authority.

Before you ask another question, consider:

What have they actually asked me to help with?

Field Notes

Read your own terrain, every Sunday

One leadership signal a week, read through the map, so you know where you're standing and what to do next.

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Catherine Insler Catherine Insler

He gave himself a deadline. Then it arrived.

A 20-year employee, a stage 4 diagnosis, and a line he'd drawn himself. This is what shows in the blog list and feeds the social preview, so it's the same hook as the email.

an empty office desk at sunset

For 2 years, a man with stage 4 cancer stayed on the company's books as a full-time employee. He hadn't been at work in over 16 months, and he wasn't drawing a paycheck. Someone had decided to keep him there.

That someone ran operations. He'd hired the man himself 20 years earlier and watched him build most of a working life at the company.

When the diagnosis came, he kept him on: active employee, full insurance, coverage that cost the company $300 or $400 a month. Nobody pushed on it at first.

Then he gave himself a line. If the man wasn't back at work by the 2-year mark, he'd sit down, have the hard conversation, and close it out. Stop the premiums, end the employment, in a way any operations leader could defend if someone asked why.

Stage 4 cancer doesn't come with a timetable. People live with it, sometimes for years, so he was setting a deadline against an outcome no one could predict.

That's the reasonable version of the job. You set a limit, you apply it consistently, and you make the decision you can explain in a room. Anyone who has managed people long enough knows that version.

Then the 2-year mark arrived.

The man still might come back to work. The operations leader didn't know that. He only knew the 2-year mark had arrived, and when he looked at the line he'd drawn, he decided it no longer mattered.

So he kept paying, and he kept the man active. He'd decided that 20 years bought something the policy couldn't measure, and that he owed some of it back.

The family called the other day. The man had died. Because he was still an active, full-time employee, his family would receive the life insurance payout, around $250,000.

This was a man who had worked for the company for 20 years. He hadn't made a lot of money, and he had never owned a home. His family didn't know the company had kept paying the premiums, or that someone had made that decision on his behalf.

When the operations leader spoke with the man's daughter, she told him she didn't know how she was going to pay for the funeral. That's when he remembered the life insurance, and he told her. There was silence on the phone. When she finally spoke, she could barely get the words out. The money would pay for the funeral, and it would help the family care for their mother now that their father was gone. Finally she said, this changes everything.

Two years of premiums came to around $9,000. A quarter of a million dollars reached a family because one person got to the line he'd drawn for himself and decided the line wasn't the most important thing in front of him.

The operations leader told me this story very casually. I told him I thought what he'd done was remarkable. He looked me dead in the eye and said, "It was the right thing to do."

I've been thinking about that ever since. He didn't wait for someone to tell him he was allowed to do it. He didn't have a policy telling him that 20 years of work had earned this man another month of coverage, and then another, and then another. He had a perfectly defensible reason to stop, and he didn't. He knew the man. He knew the history. He knew what was at stake. When the rule he'd made for himself finally collided with what he believed was right, he trusted what he knew.

Maybe that's what permission is. You already know the right thing. You just stop waiting for someone to tell you you're allowed to do it.


If you want to understand the pattern underneath what keeps repeating for you, the Source Assessment maps which pathway you lead from under pressure, so you can see the identity driving the pattern.

Take the Source Assessment

That operations leader trusted what he knew about himself under pressure. The Source Assessment maps the same thing for you: which pathway you lead from when the defensible call and the right call pull apart.

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managing up map Catherine Insler managing up map Catherine Insler

Are you being asked to take on more?

an image of the the oregon coastline

It rarely starts as a new job.

Someone leaves, and you cover the gap. Your team grows. A project that used to belong somewhere else lands with you. Your boss asks you to take ownership of something because you are good at it.

You start attending meetings you were not in before. Making decisions you did not used to make. Carrying relationships, problems, or outcomes that once belonged to someone else.

‍ At first, it may make sense. The work needs to go somewhere. You can handle it. Maybe you even want the opportunity.

But then a few months pass, and the temporary responsibility is still there. The project has become part of your normal work. Nobody has taken anything away. Your title has not changed. Your job description has not changed. Your compensation has not changed.

You are doing more.

The question is whether your job has changed.

‍More work is not always a bigger job

There are seasons when almost every manager carries more.

A busy quarter. A colleague on leave. A difficult launch. A short-term vacancy. A project that needs temporary leadership.

That can mean more hours, more pressure, and more work without changing the underlying value of the role.

‍There is another kind of "more."

You become accountable for another function. Your span of responsibility increases. Decisions that once belonged above you now belong to you. You inherit a team, a budget, a customer relationship, a process, or an ongoing business result. The complexity or consequence of the decisions you make increases. Work that was supposed to be temporary becomes permanent.

‍The shape of the job is changing.

‍And when the organization permanently changes the job, the agreement around the job deserves to be reconsidered too.

Start by locating what changed

Before deciding whether you should ask for more money, get specific about what has actually been added.

Look back six months.

What are you responsible for now that you were not responsible for then? Not just tasks.

Look for changes in:

Scope. Are you responsible for more of the business?

‍Accountability. Are there new outcomes you are now expected to answer for?

Authority. Are you making decisions that previously belonged to someone at a different level?

Span. Are you responsible for more people, locations, customers, vendors, budgets, or functions?

Complexity. Are you coordinating across more parts of the organization or solving problems with greater consequence?

Risk. Are you carrying decisions where getting it wrong now costs the organization more?

Those changes tell you much more about the job than the length of your task list does.

Then find out why

This is the conversation managers often skip.

They accept the additional responsibility and try to prove they can carry it. But you need to know what leadership thinks is going on.

Is this temporary coverage? Is it a developmental assignment? Is the company redesigning the role? Are you being prepared for promotion? Did another position disappear and its responsibilities move to you? Or has the work simply migrated toward the person most likely to make sure it gets done?

Those are different situations. And they should not have the same agreement around them.

If the answer is temporary, ask for the end point. If the answer is development, ask what you are being developed toward. If the answer is a permanent expansion of the role, it is time to talk about the role itself.

A useful distinction: Temporary work has an end point. Developmental work has a learning purpose. Permanent expanded work needs a new agreement.

Without those distinctions, "Can you take this on?" turns into "This is yours now."

Pay attention to what did not move

When responsibility changes, several other things may need to move with it.

Your job description. Your decision rights. Your title. Your goals. The resources available to you. What comes off your plate. And, yes, your compensation.

Organizations do not always move those pieces together. You can receive more accountability without more authority. A better title without better pay. More people without more support. A "development opportunity" without any defined destination. Or a permanent increase in scope that is still treated as temporary because nobody has made the change official.

That mismatch is the thing to look at.

Field Notes

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One leadership signal a week, read through the map, so you know where you're standing and what to do next.

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So, is a raise warranted?

Ask for a review when the job itself has gotten bigger, not when the week was hard.

Ask yourself:

Has the additional responsibility become ongoing? Has the scope or complexity of my role materially increased? Am I accountable for outcomes I was not previously accountable for? Am I making decisions at a higher level of consequence? Would the organization have to hire at a different level if it were filling the job I am actually doing today?

If the answer to several of those questions is yes, you have a reasonable basis for asking the organization to review both the role and its compensation.

A raise here is recognition that the organization is now asking you to perform a job with greater value, responsibility, complexity, or consequence than your current agreement reflects.

Bring the changed job into the room

This does not have to be an adversarial conversation. Your job is to make the change visible.

Instead of: I've been doing so much more and I think I deserve a raise.

Try locating the terrain: When I look at my role compared with six months ago, several responsibilities have become permanent. I'm now accountable for ___. I've taken ownership of ___. And I'm making decisions about ___ that weren't previously part of my role. I'd like to review my job description, level, and compensation against the job I'm actually performing now.

Then stop.

Let them respond to the actual change.

Maybe there is context you cannot see. Maybe the responsibility really is temporary. Maybe a promotion is already being considered. Maybe compensation cannot move immediately. Maybe leadership does not realize how much of the abandoned work has accumulated with you. Or maybe you find that leadership expects you to keep carrying the expanded role indefinitely without changing the agreement.

That is information too.

You do not have to decide what to do with it in the same conversation. But now you know where you are standing.

One thing to carry

Being capable of carrying more does not automatically make the additional work yours.

Before the extra responsibility becomes normal, read what changed.

What was added? Why was it added? How long is it supposed to remain? What authority came with it? What left your plate? And what changed in the agreement around your role?

Because if the organization has permanently changed the job, it is reasonable to ask why the agreement around the job has not changed with it.


If this is the terrain you're standing in, where the job got bigger and the agreement stayed the same, the next move is the conversation with the person who can change the agreement. Managing Up maps how to bring the changed job to them so they can act on it.

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