Your middle managers are the lifeblood of your organization. And it’s you, as a manager of managers, who keeps that blood pumping. 

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Yet with more than half of managers feeling burned out at work, there’s no way they can be as effective as they need to be for their respective organizations to flourish.

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Take a look at your own organization and at the managers you oversee directly. Are they burnt out and overworked? Are they adequately supported and given the resources and training they need? Are their team’s suffering as a result? 

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If yes, you may start to wonder how you can better support them so that they grow into their management role and lead effectively. 

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Don’t worry, we’re not the type to highlight a problem without offering a solution.

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In this short guide, you’ll learn:

• What your role is as a manager of managers and how it differs from other managers
• Why supporting your middle manager is important for business success
• 7 practical and actional ways you can help your managers lead
• The needs of first-time managers vs experienced ones

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What’s the difference between managing managers and managing individual contributors?

Prioritization, active listening, and empathy are just a few key management skills all great managers need.  

But with each management type, comes nuances you need to account for.

What types of management roles are there? JooBee Yeow, advisor to start-up founders and leadership expert, outlines 4. 

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1. Managers of specialists (or individual contributors)
2. Managers of managers
3. Managers of functional strategy
4. Managers of business strategy

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In this guide, we’re focusing only on the differences between managers of specialists/individual contributors and managers of managers.

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A manager of specialists is like the captain of a ship. Their primary concern is the sailors (their team members) on board, ensuring they're well-trained, motivated, and working cohesively. 

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They're setting the course (strategy) for that one ship and planning the next three months, ensuring that every individual contributor is aligned and contributing effectively.

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But as a manager of managers, you’re not captain anymore, you’re the admiral. And instead of guiding one ship; you're setting the course for an entire fleet. 

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Your focus isn't on the individual sailors but on the captains who lead them. Your role is to ensure that all the ships, under the guidance of their respective captains, sail in harmony towards a common destination. 

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This requires a broader vision, planning 3-6 months out, and coordinating the efforts of multiple teams toward shared goals.

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Going from manager of ICs to a manager of managers requires a mindset shift. 

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As JooBee Yeow says, you go from ‘how do I enable my team to perform?’ to ‘how can I align and influence multiple teams to achieve collective goals?’ 

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Here's where the real challenge—and opportunity—lies for managers of managers: growing the people management skills of the managers you oversee so that they can organize their team to focus their efforts effectively. 

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You don’t need to make your managers better at marketing, or product, sales, engineering, or whatever industry they’re in. You need them to be better with people—to know how to motivate them, push them, support them, and develop them. 

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Also worth knowing: Managers of managers can be members of the leadership team at small organizations but they may be a tier below at larger ones. The hallmark isn’t in where they are but what they do, who they oversee, and what their expected impact is. 

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Why bother?: The impact people management has on business performance

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It’s a tale as old as the start-up world itself: a high-performing individual contributor (IC) delivers consistently impressive results, and as a reward, they're promoted to a managerial position.

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Only, excelling as an IC doesn't automatically translate to being an effective manager. 

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Without the right resources or training, these first time managers find themselves floundering, unsure of how to navigate their new responsibilities, and losing confidence in their abilities by the day. 

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Their team suffers too. In fact, 75% of participants from a McKinsey survey say the most stressful aspect of their job is their immediate boss. 

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That’s because most managers aren't equipped to lead effectively, and the consequences of that ripple throughout the organization.

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Teams become disjointed, morale plummets, and productivity takes a nosedive. The end result? Missed targets, increased employee turnover, and a tarnished company reputation.

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The good news is that if managers can do that much damage, they can also be a catalyst for good.

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By investing time and effort into upskilling and supporting managers, you can boost team cohesion, drive productivity, and foster a positive work environment.

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A 2023 Perceptyx report shows that compared to those with a bad boss, employees with a great boss are:

• 2.5x more engaged
• 5x more likely to handle workplace stress
• 12x more likely to cooperate with colleagues 

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So the equation is simple: better managers lead to better business outcomes. 

All that’s left to do is make them great leaders. And to do that, you need to be a great leader too. 

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7 tips for managing managers effectively

You might be new to this role and previously managed ICs, or you might have been at this for a while and simply want to get better.

In truth, it doesn’t matter because our advice to you is the same. 

To make sure you're on the right track, here are 7 actionable tips:

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1. Set clear expectations
2. Make time for one to one’s with them and their direct reports
3. See their leadership in action
4. Give them regular, timely feedback  
5. Become their mentor and coach
6. Recognize not everyone wants to be or should be a manage
7. Use Waggle – the AI co-pilot that helps managers (of managers and ICs!) lead

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1. Set clear expectations

One thing should be clear by now; effectively managing managers requires a different approach than managing individual contributors.

But every employee from top to bottom, left to right can perform better when they have clarity over what they do and what’s expected of them. 

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Give managers who report to you a clear roadmap. Start by outlining their key responsibilities, the goals they should aim for, and the metrics by which their performance (and their team’s performance) will be evaluated.

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For example, if you're focusing on improving conversion rates, don't just set a blanket target. Specify that you expect the manager to identify areas of improvement in the sales process and coach their team on best practices.

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This emphasizes the manager's role in guiding, training, and uplifting their team to achieve those results. And they'll come in handy when it's time for formal performance reviews because no one will be in the dark as to what they were meant to do.

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Some resources that can help is our new manager checklist and this guide with new manager tips that will help them understand the nuances of their role. Pass them on to the managers reporting into you, especially if they're new to their roles.

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2. Make time for one on one meetings (with them and their direct reports)

The higher you climb in an organization, the more meetings you get pulled into and the more pressed you are for time. Calls will overrun, fires will pop up that only you can put out, and lunch breaks have long gone. 

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You’ll be tempted to cut things where you can and find yourself thinking, 'I spoke to [insert name of direct report] last week, I can cancel today’s 1-1.’

But that’d be a mistake. 1-1s are invaluable, offering insights into their wellbeing, challenges, needs, and achievements. They let you know if they’re struggling to cope with their role, what problems the team is facing, and how you can support them. 

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Occasionally, take the time to connect with their direct reports as well. 

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This isn't about bypassing the manager but about building a holistic understanding of the team's dynamics. By engaging with these team members, you can gain first-hand feedback, understand the on-ground challenges, and appreciate the impact of the manager's leadership style.

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Need help preparing for and running one on ones? Grab our free template.

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3. See their leadership in action

When managing managers, you can’t just take their word for how well they’re getting on. They might have blindspots only you can see. But you’ll never see them if you don’t see them in action.

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You need to witness their leadership styles firsthand. Observing how they interact with their team, handle conflicts, make decisions, and motivate their members can provide invaluable insights into their effectiveness as leaders.

Join team calls and brainstorming sessions or have them record some of their calls (with permission from all involved). You can watch the call later and make notes about where they could have handled something differently and what they’ve done well.

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This hands-on approach allows you to offer timely feedback and guidance, ensuring that the managers under your wing are continuously growing and refining their leadership skills.

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4. Be their mentor and coach

When you manage managers, you need to both mentor and coach. You can even role play difficult management scenarios your manager is facing. Maybe they have a difficult conversation coming up that they don’t know how to handle. 

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As a mentor, share your experiences, insights, and wisdom, guiding them through the complexities of leadership. 

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On the coaching front, focus on actionable feedback. If a manager struggles with delegation, for instance, provide them with strategies and techniques to improve. If they're excelling in team motivation, acknowledge it and discuss ways to further enhance that skill.

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5. Give them regular, timely feedback

Effectively supporting your managers means not letting them navigate alone. And that requires regular, timely feedback. 

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This goes hand in hand with your mentorship and coaching responsibilities.

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After a team presentation, don't wait for a quarterly review to commend their effective communication or suggest improvements. Address it promptly, allowing them to immediately build on their strengths or rectify missteps.

But don’t forget to follow the golden management rule: praise in public, criticize in private. 

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You also want to seek feedback on your own leadership to make sure you’re supporting them in the ways they need as much as they’re leading their team to high performance.

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6. Recognize not everyone wants to be or should be a manager 

One of the best ways to support your managers is to know who is suited to the role and who isn’t and hire or promote accordingly.

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You see, not everyone is cut out for a managerial role, and that's perfectly okay. 

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Some individuals thrive when they can dedicate their time to IC tasks, relishing the opportunity to be experts in their field. The transition to people management can sometimes dilute that passion.

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Be sure to have candid conversations with potential managers about their aspirations and concerns. While the allure of a promotion can be tempting, the reality of managing might not align with their strengths or interests. 

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And sometimes, they won't realize this mismatch until they're knee-deep in managerial duties. 

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By fostering open communication, you can ensure that those stepping into leadership roles are genuinely enthusiastic and equipped for the challenges ahead. If they change their mind about the role, they should feel comfortable telling you. 

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7. Get and give access to Waggle – the AI co-pilot that helps managers  (of managers and ICs!) lead

Senior managers like you and middle managers like the ones you manage juggle countless responsibilities. 

But what if there was a management tool designed specifically to streamline your tasks and elevate your leadership skills?

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Waggle is that tool. It’s an AI co-pilot that lets you manage your work, your team’s work, and your team in one place. You can use it to offload admin and stay on top of tasks while your managers use it to improve their leadership skills and feel on top of their responsibilities.

Waggle is there to coach and support them in the moments you can’t. 

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→ Sign up to a free 15 day trial and get your team onboard—it only takes minutes to set up. ←