The Executive's Guide to Maximizing Middle Manager Potential
As a founder, CTO, or higher-level executive leading organizational growth, you've likely encountered the need to bring in managers and technical leaders to free up your operational load. Someone experienced, with leadership skills, who can hit the ground running.
These moves are no brainers and allow the ability to shift your focus from day-to-day operational tasks to more high-level, strategic responsibilities. However, you may find that things aren’t progressing the way you expected, and you need to dive in again.
Suddenly, you’re facing questions like:
How do you get the most out of the money you’re spending on them?
How can you work effectively with them, when you don’t have as much experience in their area of expertise as they do?
Worth mentioning: If they’re worth their money, they’ll help you with this part! But there are things you can do to make your partnership even better. - And most of all:
Now how do you help them shine?
Let’s face it — effectively managing and maximizing the potential of these key hires is challenging. In this guide, I'll explore strategies, tips, and frameworks to help you get the most value from your investment in experienced managers, all while empowering them to be happy and high-performing.
A note on middle managers
Middle managers play a crucial and often underestimated role in organizations. Positioned between top-level strategy and daily tactical execution, they bridge the gap between your vision and the team's day-to-day operations. While it's tempting to leave them to "figure it out” on their own, actively engaging with your middle managers can significantly enhance organizational alignment.
Ensuring you are creating space for aligning expectations, continuous communication, open decision-making, and professional development is key.
I get it. You’re busy! That’s why I’ve put some of the most effective practices that have worked for me, my teams, and my clients over the years, all in one place, just for you.
Define the interface between you and your middle managers
You may be familiar with APIs. Think about your interactions with your direct reports like you would about designing an API: Make intentional decisions about how you design your partnership.
Here are examples of what this can look like, and how to get started, based on four key principles from Jakob Nielsens’s heuristics for interaction design:
Interface Design Heuristic #1:
Visibility of System Status
“The design should always keep users informed about what is going on, through appropriate feedback within a reasonable amount of time.”
Visibility is critical, and, in my experience, is the root cause of >80% of organizational issues.
Disseminating information with your middle managers, and vice versa, is a delicate dance. You still want the information you need on a regular basis to have a good sense of what’s going on, while staying (or just getting!) out of the weeds. Here’s how to design your interactions with high visibility in mind:
Get visibility about the team(s) rolling up to your middle manager and check your alignment
I recommend creating a structure around the visibility that you need - organizations run on a cadence and it helps a lot with visibility to create a habit of sharing information regularly and consistently.
How: Ask your middle manager to put these updates into writing - one, because it’s good practice, and two, because it means you can use your synchronous meetings for more valuable conversations than status updates. Here’s a tried-and-tested approach for how to do this (with a template!).
When: I usually ask the middle managers on my teams to send me info about their teams every Friday by the end of their day.
Give visibility
Here are four helpful ways you can enable effective transparency across your teams and organization:
Lead with context
Your middle managers need as much context as possible to be ready for where your organization is headed. Prioritize context around where directives are coming from, new project shifts, or if a project is shutting down. Your direct reports typically already ask you what they expect they will be asked from their employees, and that’s a really useful thing, especially when in doing so you realize you overlooked something.
Address why things are happening, and be prepared to answer hard questions.
How and when to communicate:
Regular weekly updates: I write an email of important organizational events and context to my management team. This includes:
Important things I’m hearing in executive meetings, in conversations with board members and investors, and at industry events
My sense of where the company is headed
! I always add a note about which of this information they can cascade
On-the-fly: I send summaries of important meetings that I’m in to the middle managers on my team. Mainly, meetings where:
Changes and decisions were made that will impact them or their team. This may seem like a nit pick, but this swift act is critical in building and maintaining trust. It’s your job to avoid them feeling blindsided by organizational changes.
New HR policies or organizational strategies were decided upon. Giving your team a quick heads up on important updates will not just build trust between you and your report, but will also set up your report for success.
Synchronous: Staff meetings and 1:1 meetings are great spaces to discuss questions or dive deeper into what these things mean for the managers and teams. The more structured, agenda-oriented, and collaborative these meetings are, the more you’ll be able to get (and give).
Invest in building a rapport
Speak with your direct reports on a regular basis. Consistent, one-to-one meetings are critical to building and maintaining trust and strengthening relationships with your managers. Aim for 45 minutes to foster meaningful discussions, 30 if you’re absolutely pressed for time.Meet at least bi-weekly, or weekly during periods of significant change. Don’t cancel these meetings unless absolutely necessary.
Some valuable ways I’ve spent my one-to-one meetings include:
Asking what topics your middle manager wants to talk about, and talking about them
Soliciting feedback and calibrating roles
Granting visibility into team budgets and metrics for enhanced ownership
Encouraging pragmatism (read how to do that here)
Let your managers own their work
Let them own their area of work. A frequent complaint I hear from executives is that they feel like there’s a low sense of ownership among their managers. To me, this is a sure sign of being stuck in an inertia trap, and often even the result of, hear me out, executives unintentionally getting in the way; more about this trap and how to get unstuck in this article: Breaking Free from the Inertia Trap: How to Get Your Team Members to Take Ownership .
Provide access to budgets and metrics. Make sure they have visibility into metrics for their area, ideally alongside the metrics of the whole organization so they have a baseline. Don’t know what metrics are most important for them? These articles can help.
Cascade information through your middle managers
I regularly run organizational performance assessments for Product & Engineering Departments, and one of the items on my checklist is how information flows through the organization. The best executive leaders make a habit of intentionally showing up for their teams (more on this below), while letting the majority of operational information flow through their managers to teams and employees.
Why should you not communicate everything directly?
Every leader can tailor communication in such a way that it lands best with their group (e.g. department, domain/set of teams, team). Leaders know their teams, and adjusting messaging will go a long way in getting everyone on the same page.
It helps to better understand what is resonating.
It builds trust from your employees in the leaders and their capabilities.
It allows the leaders on your teams to ask questions before sharing news onward.
How to do this: You communicate to your middle managers; they pass information onward from there. Feedback flows back to you the other way round, from employees, through middle managers, to you. That’s all!
Interface Design Heuristic #2:
Match the System and the Real World
“Follow real-world conventions, making information appear in a natural and logical order.”
It takes a lot of intentional work to grow your own skills as your organization grows. A lot of leaders don’t have time, so here are practical steps that I’ve seen work well:
Get out of the critical path, stop being a bottleneck
You’re probably still involved in work that you can’t or shouldn’t be doing anymore. Classic examples are: Incident response, customer handling, software development.
Work with your middle managers to get out of the critical path for this work as quickly as possible. Your organization and your future self will thank you.
Define and evolve your roles & responsibilities together with your middle managers
It’s likely that neither you nor your middle managers have clearly shaped roles, and that your roles will need to evolve over time as organizational needs change.
Here are two approaches I found work well to make this explicit:
Abstract approach: Ask your middle managers to come up with a definition for their role
and review it together. Some leadership teams do well with this approach, but many struggle with it: It’s often easy to agree in the abstract (“I own processes, you own strategy”), but the breakdown and stepping on each others’ toes tends to happen at a much more tactical level in the day-to-day work (“I thought I owned processes, why do you suddenly want to get involved?”). Therefore, you may try the second approach:
Descriptive approach: Ask your middle managers to document their recurring work. Use these notes to identify patterns and come up with a role description. I found that this approach often helps leadership teams ground their role conversations more in the organization’s actual needs and the real daily work. Plus, this lighter-weight setting makes it easier to iterate over time.
No matter which approach you choose, iterate together over time → see more under “Calibrate.”
Leaders work most with their “first team” of peers - not their direct reports
The most successful leadership teams work more closely with their peers than with their direct reports. This includes:
The managers and leaders reporting to you. Encourage them to work together closely; here’s how.
You. In the same vein, your primary team should be your peers; here’s how you can get there.
Interface Design Heuristic #3:
Consistency
“Users should not have to wonder whether different words, situations, or actions mean the same thing. Follow platform and industry conventions.”
Say what you expect
Being explicit about what you expect reads simple and you may think it goes without saying. In my experience though, this is something a lot of us really struggle with. Often times, we don’t know where to start, and expectations are often difficult to formulate in the abstract, so here’s my go-to list:
Tell them when something is urgent
Ask questions before judging. Approach any situation with curiosity before judging.
Detail: Avoid “why?”-questions
Delegate problems, not solutions or how you want problems to be solved. When youexpect something specific, say it. When you want specific work done or something specific to happen, tell them.
Set clear goals and be less afraid of saying no
Middle managers are often carrying the main burden in chronically overloaded organizations, which, even with the most capable of managers, never succeed to the degree they want to. Here’s how to do better:
Actually focus. Strategy is an implicit decision about what you’re not doing. If you overload your teams with “focus areas,” inevitably not everything will get done, but in this case, fate will decide for you. Own that decision.
Make sure goals are clear to everyone involved. A good way to test this is to ask each of your reports to come up with goals for their team that they believe are aligned with these goals.
Align on priorities. Get on the same page on what goals and work are actually important.
Break bad habits. It’s tempting to throw some high-level goals their way and say ‘they’ll figure it out’ (I know, I’ve done it), but resist this urge!
I understand that this is really hard for a lot of teams. If none of this is possible, I recommend asking yourself why that is and what makes you think that this can’t be changed. Middle managers not having access to or ownership of information will inevitably lead to poor decisions and misalignment, and will make your life and theirs so much harder than it should be.
Interface Design Heuristic #4:
Recognize, Diagnose, and Recover from Errors
Calibrate
Especially if you’re only newly working together, you likely need to calibrate to each others’ communication and working styles. Make a habit of asking lots of questions to understand, and give feedback as often as you can.
Specific feedback: As quickly as possible, to help you both calibrate and align.
General performance feedback: At least monthly. Put a reminder to exchange
feedback into your 1:1 template or add it to the calendar event.
Role calibration: Anticipate that you’ll need to clarify the boundaries between your roles over time. You’ll likely accidentally step on each others’ toes from time to time, and if your company is changing a lot, this may even remain a frequent issue. See more about this, and how to fix it, under “roles and responsibilities.”
Handle errors gracefully & hold managers accountable
When was the last time you overrode a decision one of your direct reports made? When was the last time you jumped in to solve a problem, or fix a critical issue?
Surprises will come. You will have cases where incidents or mis-handlings happen that you weren’t aware of. There will be issues in your interface with your middle managers; you’re (likely) both human, after all.
Accountability doesn’t mean firing them on the spot when stuff is going wrong. A very revealing question I love to ask: “What happens in your company when goals aren’t met?” This question may be worth thinking about more.
Here’s how to hold your manager accountable and what to do when goals aren’t met, or other things go wrong:
We talk about it. Run incident reviews (also known as “postmortems”), retrospectives.
We extract lessons learned from what went wrong.
We make space and time to address these lessons we learned.
It’s impossible to really prevent all errors, but it is possible to recover from them quickly and with more clarity. Here’s how to do so:
Recognize, diagnose: When things go wrong, talk about it as quickly as possible. Whenever you override a decision that your direct reports made, or have to “dive in” to do things that you’d expect them to do, treat it as an incident: Review together what happened, and what your direct reports could have done to prevent this. These instances can provide really important information. Try to genuinely understand where the misunderstanding or mismatch in expectations came from. You may ask things like:
“I would have expected xyz to appear in your weekly update to me. What made you decide not to include it at the time?”
○ “I was surprised that the team wasn’t aware of x. What happened there from your point of view?”
Recovering from errors: Talk about what you learned from things going wrong, and how you’ll act differently in the future.
Be the culture. Be accountable and dependable yourself. Follow up on what you commit to.
More on creating accountability in your organization:
How to create accountability in your engineering organization
How to increase accountability while you build high-performing teams
Now that you have a clearer picture of how you and your middle managers work together, let’s talk about what this means for you and how you...
Show up as a leader for your organization
Show up as a leader for your organization, visibly. Your job is to be the connector to your organization and the “outside world”, i.e. investors, customers, as well as the higher-level leadership team.
To show up strong in this arena, run department meetings yourself, at least monthly, I recommend around an hour. If you’re running a high-growth or high-change team, it can be worth running these meetings every two weeks for an hour. Use these meetings to make the connection for your teams with the “outside world” and talk to them about:
Strategy. This should be your number 1 recurring agenda item. Strategy is your job, tactics are your employees. They don’t think about this as much or as often as you do, and you will need to talk about it as much as you can. And yes, you will get tired of saying it. That’s the tough part about being an executive.
Progress on organizational and company goals
Broader context. Things like Important industry changes, reports or research, or observations you’re making and how it maps back to your strategy and vision.
Higher-level topics. A former boss of mine used to sometimes spend the first 5 minutes of this meeting talking about a very high-level topic, e.g. the impacts of the pandemic on our teams. These messages were often really powerful in setting the tone for our meetings. It re-oriented everyone and helped team members understand that those topics were on our minds as leaders, and what they meant for us.
In these department meetings, make space for others:
Your teams can talk about exciting new projects, lessons learned, or swap success stories.
The managers reporting to you can present organizational initiatives.
Stakeholders and partners like product managers can “guest star” and talk about the roadmap.
By the way, if you run an engineering department in a product company, I recommend running such a meeting in conjunction with your product department as a “delivery meeting,” instead of an engineering-only event. This will help build the partnership.
Showing up as a leader for your organization also means actively leaving space for others. In practice, this can mean that you reserve 10-15 minutes for your high-level topics, and leave the rest of the time to others.
For more details, check out a helpful (and free!) onboarding checklist here.
Your middle managers are more than just intermediaries between your leadership team and employees on the ground. Equip them with the context, ownership, and clarity they need, and you will not only empower them, but also enhance the overall productivity and morale of your team. Middle managers bring so much to the table. Setting them up for success will play a critical role in unlocking your organization’s excellence.
