← Ideas · Field note 007
It's tough in the middle.
Middle managers deliver, lead and translate, often all at once. A field note on designing leadership development for that reality.
- Deliver
- Business outcomes, priorities and decisions
- Lead
- People, performance, development and relationships
- Translate
- Organisational direction, change and expectations
The middle
Middle managers carry several responsibilities at once. They're accountable for business outcomes. They lead and develop people. They translate organisational priorities and change into something a team can act on.
Those responsibilities often compete for the same hour, and there's rarely a tidy way to give each one what it needs. Leaders make judgement calls about what comes first, and different leaders make different calls, usually for good reasons.
That's the reality leadership development has to design for. We tend to be clear about what we want leaders to do. We're less consistent about where, and how often, they get to try it.
Leadership development has to work in the middle of all that.
Translate the brief into a moment
Find the moment where the behaviour matters.
Leadership briefs usually arrive as a broad statement. "Our leaders need to be better coaches." It's a reasonable thing to want, and too broad to design for.
The brief
"Our leaders need to be better coaches."
The moment
A team member brings a problem to their 1:1.
What might be happening nowWorth checking
The manager, keen to help and short on time, solves it for them.
What good looks like
The manager asks a few useful questions, listens, and helps the person decide their own next step.
Good leadership also means knowing when to coach and when to give a clear steer, particularly when time is short or the risk is high.
Before deciding what leadership development to design, identify the moments where leadership behaviour needs to improve.
Then understand what people are expected to do, what happens now and what good would look like. A moment is something you can watch for, ask about, rehearse and notice improving. The intervention can wait until you know.
Leadership moments worth investigating
- Coaching someone through a problemAsks before answering.
- Giving difficult, constructive feedbackSpecific, timely and still respectful.
- Delegating meaningful responsibilityHands over the decision as well as the task.
- Navigating disagreement or conflictMakes the disagreement safe to discuss.
- Making decisions under uncertaintySays what's known, decides, and revisits.
- Supporting people through changeExplains what's known, what isn't, and when there'll be more.
- Addressing a performance concernRaises it early, with specifics.
- Developing someone towards a new responsibilityCreates stretch, and stays close enough to help.
The leader, the work and the environment
What's stopping it happening consistently?
Leadership behaviour is shaped by three layers that pull on each other. The same visible gap can come from very different places, and often from more than one.
The environment
The work
The leader
- The leader
- Knowledge, skill, confidence, judgement and experience.
- The work
- Responsibilities, routines, workload, time and chances to try things.
- The environment
- Expectations, their manager's behaviour, culture, incentives, systems and support.
- 1Skilled, but no roomThe leader can do it. Their week rarely leaves space to.
- 2Supported, but unrehearsedThe conditions are good. They need realistic practice with a hard situation.
- 3Several at onceA gap in one layer often shows up because of another.
Investigate before settling on a cause.
- Can they do it when the situation is easy? If so, skill may not be the main issue.
- Do they still do it when the stakes are high, or the conversation is uncomfortable?
- When did someone last see them do it well, and what was different?
- What in a normal week pushes it out?
- What does their own manager notice, ask about and reward?
- What does the evidence say, beyond what people assume?
Not every gap is a training need, and not every gap belongs to the organisation. Let the evidence decide.
Where leaders practise
From the work to the room, and everything in between.
Leaders can build skill through the work itself, through protected experiential development, or both. They're complementary. Depending on the situation, combining these approaches with coaching and feedback can be particularly effective.
In the workAway from the work
In the work
Everyday coaching
Ask better questions in the 1:1s a leader already has, with someone who occasionally observes, gives feedback and prompts a short reflection.
A combination
Leading through change
Scenario work and peer discussion before the change lands, application with the team, then follow-up with their own manager.
Away from the work
Difficult performance conversations
Realistic rehearsal, more than one attempt and facilitated feedback before the real conversation with a real person.
The conditions
Understood, but hard to sustain
Sometimes the gap sits below the line, in the work around the leader. They know what's expected and they can do it, yet the behaviour fades because something in the system makes it hard to keep doing. More development on top rarely holds until those conditions change.
01Observe
- What their own manager asks about, notices and rewards
- Whether 1:1s and team meetings leave room for it
- Workload and timing in a normal week
- Targets or incentives pulling the other way
02Fix
- Brief their managers to ask about it and reinforce it
- Build it into routines that already exist
- Make leadership expectations realistic next to delivery targets
- Change what gets noticed and recognised
Rehearsing the high-stakes moments
A safe place to get it wrong first.
Some moments are too consequential to learn live: a first serious performance conversation, a team hearing news they won't like, a decision with no good option. This is where protected rehearsal earns its time, with realistic simulation, a skilled facilitator, more than one attempt and feedback specific enough to change the next one.
Leaders arrive with a moment from their own work they want to get right.
Rehearse under realistic pressure, get specific feedback, try again.
Someone notices it, and supports the next one.
An AI practice coach
More rehearsal before the real conversation.
AI can give leaders more chances to rehearse, get feedback and improve before the conversation that counts. A practitioner can set this up once as a reusable coach, a saved prompt or skill file, so leaders get the same approach every time.
Leadership practice coachReusable prompt
Act as my leadership practice coach. First, ask what conversation or behaviour I want to practise, what I'm finding hard, and what a good outcome would look like. Help me set up a realistic fictional scenario. Then play the other person and respond naturally. Don't make it too easy. Afterwards, give me specific feedback on my approach, the questions I asked, how I listened and how clearly I raised the issue. Then let me try again.
Practise a conversation
CoachWhat do you want to practise, and what's hard about it?
LeaderRaising a missed deadline with someone who's usually reliable. I tend to soften it until it disappears.
Coach, in role"I know it's late. There's been a lot on, and I didn't want to keep asking for help."
Coach, feedbackYou named the deadline clearly this time. Then you moved straight to a new date. They mentioned asking for help. Try exploring that first.
Use tools your organisation has approved, keep names and confidential employee information out, and leave decisions about people with people.
From one leader to many
A skill in one leader. A habit across many.
Building leadership maturity takes more than teaching the same skill to more leaders. A behaviour becomes normal when the people and routines around each leader keep reinforcing it.
- Their manager asks about it and gives feedback
- Peers practise and compare notes
- Routines build it into 1:1s and team meetings
- Feedback from the team, over time
- Working conditions leave time to do it
For a practitioner, that means designing beyond the development experience. You may need to influence what managers ask about, how peer groups work, the rhythm of 1:1s and team meetings, whether leadership expectations are realistic next to delivery targets, and how progress gets noticed.
Evidence
Look for it in the work.
Attendance, completion and satisfaction tell you useful things about the development experience. They can't tell you whether leadership has improved. For that, look at what's happening in teams.
- Are leaders asking better coaching questions?
- Are difficult conversations being handled more skilfully?
- Are managers giving useful feedback?
- Are people being given real ownership, with the right support?
- Are leaders better prepared for consequential situations?
- Are managers reinforcing the behaviours across their teams?
Look for patterns in behaviour and feedback over time, from more than one source.
The takeaway
Find the moment. Investigate the barriers. Make room to practise.
To close
We're asking leaders to get better at leading.Have we made room for them to practise?