Leadership Development: How to Promote and Grow Your Management Team

According to several independent studies, 80% of leadership positions have no formal training at all.

If you run a mid-sized business and promote your management team internally (as the majority of the organizations out there), you likely fall into the majority of the businesses that grow organically. Management, along with leadership, is often taught “on the job”—without an MBA degree or background in economics to help you move forward.

Leadership training can help people. Your staff will become more aware of their weaknesses and strengths.

Communication skills—along with other critical soft skills for leaders—are improved by learning to clearly express thoughts and feelings internally, providing and receiving feedback, and navigating business responsibilities across the board.

Critical thinking skills are learned to objectively evaluate situations. Managers who develop the skills to delegate, motivate, and reward employees are more effective. They gain a better sense of purpose, stay longer on the job, develop leaders internally, and keep the organization intact.

What Is Leadership?

The simplified dictionary definition of leadership is “the action of leading a group of people or an organization.

However, merely sitting in a corner office and handling tasks back and forth is far from instilling the leadership practices that media favorites like Jeff Bezos, Elon Musk, or Mark Cuban carry along.

Different leadership styles exist. Over time, serial entrepreneurs may morph between styles, depending on the organization they operate in, the rest of the senior management team, and the paradigms of work. What works in a creative digital agency won’t be applicable while running a factory.

The New Context of Leadership

In modern times, especially in digital-based environments, true leaders possess a number of qualities, often being referred to as:

  • Knowledgeable
  • Empowering other leaders
  • Trustworthy
  • Resilient
  • Highly experienced
  • Charismatic
  • Critically thinking
  • Innovative

Getting the buy-in from the rest of the organization is contingent on a number of factors. And when it comes to recruitment, it’s a two-way street: hires are just likely to gauge the leadership team (and the sustainability of the organization) as their ability to pass the interview cycle.

In order to scale successfully, you need trustworthy leaders able to carry the mission internally.

Leadership Development 101

A recent study shows that most of the M&A activity in 2008 was among companies with less than 500 employees. Most small and mid-sized companies don’t have the internal resources to develop the leadership skills needed to compete effectively in today’s marketplace.

There is no clear path to developing successful leadership practices internally, either.

  • Different leadership styles exist – and while there are common best practices for each, there’s no “cookie-cutter approach” that works everywhere
  • Every industry comes with different leadership expectations—and sometimes, a certification or a degree are required for compliance reasons
  • The company size matters
  • Leaders need to fill in different gaps – it may be easier to identify these and work vertically
  • Executive coaches exist – but executives don’t know how to find them or whether the process would be fruitful

This is why the prevailing leadership development approach is “trial and error”. Experience is developed over time, but companies work in a dynamic environment and there is rarely enough time for experiments.

Management vs. Leadership

According to a recent study by a Harvard Business School professor, today’s companies are eight times more likely to be disrupted than the companies from 1900 to 2000.

The main driver of long-term corporate success is disruption. The future of your company depends on you having the right skills. If you don’t, you will be left behind by the wave of change sweeping over the economy.

As defined in an HBR essay:

Management consists of controlling a group or a set of entities to accomplish a goal. Leadership refers to an individual’s ability to influence, motivate, and enable others to contribute toward organizational success. Influence and inspiration separate leaders from managers, not power and control.

This is a clear separation that stands in the way of the majority of the organizations out there.

Companies with an autocratic leadership style often enforce inheritable practices to their own teams.

Think about a fast-food chain or supervisors in low-end call centers. By large, management is about control, strictly sticking to requirements, extending to “power play” – which leaves little to no room for creativity or innovation, or motivation for growing further within the organization.

Successful leaders do empower their own team.

The first KPI I set for my own management team is creating demand for their own skills.

I firmly believe that managers should not breathe down everyone’s neck and micromanage every step of the way. Instead, they should empower their team, support them in areas they can’t excel at, develop their skills further, and have their expertise being “sought after”.

If a supervisor is on a leave, the team should feel the urge to call them – not because processes are broken, but instead, their leader is missing, and the team is incomplete.

This is what differentiates a mediocre manager from a true leader. But in order to create these leaders, you need to employ the right coaching strategies to find, nurture, and promote them.

And once you get there, it’s time to raise the bar and work toward independent decision-making and leading the way. Here’s my own leadership development framework for developing your managers into independent leaders.

Leadership Development Framework

1. Develop an Objective-Based Business Strategy

While often neglected, developing mission and vision statements is integral to pushing the organization forward. They serve as powerful tools both internally, and externally (in closing business and converting new recruits).

But the bigger picture is vague. Pushing toward a goal works backward. You reverse-engineer the final destination and form milestones that are easier to follow, and further break them down into action items.

Business strategy frameworks out there recommend roadmap development which could be anywhere from 1 to 10 years long. Regardless of the duration, the road to success should be well-defined.

Work on developing an actionable roadmap that makes sense. Similar to the old interview question of “Where do you see yourself in 5 years?”, ask yourself the same when it comes to the organization.

  • Are you aiming for a massive enterprise?
  • Is profitability the only thing that matters?
  • What are the key culture pillars you need to hire against?
  • Is there a product line that should be prioritized heavily?
  • Are there any charity initiatives the business should support better?
  • Does the onboarding process facilitate where you need to grow?

Figuring out the “bigger picture” questions would help you define a clear strategy in a similar fashion to New Year’s resolutions.

2. Break it Down Into OKRs

If you aren’t familiar with the idea behind OKRs, they represent Objectives and Key Results.

Progressive organizations like Google heavily depend on breaking down their long-term plans into quarterly goals with a number of objectives.

Regardless of whether you pick OKRs as a management technique, SMART goals, 4DX, or simple KPIs, the idea is to pinpoint more complex activities that your leadership team needs to support you in towards the bigger vision.

Examples of objectives are:

  • Growing the profit margin
  • Hiring and onboarding a new product team
  • Increasing rates
  • Become a top brand at the largest recruitment chart

Traditionally, objectives are inspiring, and broader. The following action items set specificity in place, which also allows an iterative process of achieving goals continuously every quarter.

The Key Results are the actionable activities the team can work on together to make this happen. For instance:

  • Close 3 new blue-chip clients
  • Hire 1 product manager and 2 senior engineers
  • Develop strategic roadmaps and a sales pitch for existing clients
  • Create two brand initiatives internally to help attract new talent and rank higher

Every objective is composed of a series of initiatives that support the bigger goal (i.e. there are multiple ways to achieve the same goal).

Leaders suggest different strategies to tackle OKRs, but the common opinion is establishing 4-5 objectives per quarter with 4 to 10 key results that everyone needs to work together on for maximum impact.

Focus is the main aspect of developing OKRs for your business strategy. Instead of combatting day-to-day fires without any vision in mind or working on different goals with no clear direction, this enables you to refine a strategy that makes the most sense for the organization.

3. Clearly Outline the Strategy Internally

Set enough time and sit with your leadership team.

Reveal the long-term strategy and the benefits for everyone once the goal is accomplished. Best-case scenario, your leadership team should be on the same page right away, but if you haven’t worked closely with everyone, keep in mind that this could backfire.

To prevent any negative effects, be prepared to pitch the vision with inclusiveness in mind. Some long-term goals may appear as a “change in direction” which would impact some teams. Misrepresenting the information may cause an internal revolt—and this is the last thing you want, especially in your management team.

So think carefully while developing the roadmap. Be prepared to present it professionally, and make the most out of pointing out the broad benefits for the entire organization.

Work backward from bigger problems the company has—such as limited budgets for training, too much stress while fighting with emergencies, and lack of R&D initiatives. Align the roadmap in a way that clearly outlines the positive effects of the change.

Then, describe the key objectives for the quarter along with the proposed initiatives to work upon. The direction may change slightly over the process—your team may prioritize other action items that make more sense, and this is okay. Find the balance between the right activities that everyone supports, as long as they take you further in the right direction.

4. Instill Regular Meetings

“What gets measured, gets managed.”

The best way to measure results is through recurring meetings, tracking progress, and enforcing micro-deadlines every week or two.

Why You Need to Set Up A Meeting

Meetings have a truly powerful effect when it comes to your leadership team.

  • Enforcing new processes is best done through iterations—one step at a time.
  • Regular check-ups ensure that the direction is followed properly—avoiding weeks spent on the wrong initiatives.
  • Accountability is really strong in group meetings. Imagine if everyone has their homework done and goals met – how would you feel underperforming while reviewing your status for the past week?
  • Executing in a results-driven environment transfers these processes further down the line. Other team members will pick up the new habits your management team develops.

Bottom line, set up meetings—and keep iterating.

5. Enforce Following Up

Counterproductive meetings are a waste of time.

But spending hours in direction or strategy—and not following up after—is a recipe for disaster.

I’ve been guilty of not enforcing follow-ups dozens of times over the years. I’ve consulted clients who didn’t follow through—and lost business opportunities.

We’ve experimented with different techniques, tools, and combinations. I crafted a new Operations role in charge of following up and making sure we can coordinate everything cross-departments.

It wasn’t sustainable since the general “buy-in” wasn’t there and the direction wasn’t crystal clear. Working on separate problems is one thing; aligning them with the broader vision carries a lot more weight.

Our latest approach to this is the Fellow App.

After speaking with the co-founders, I learned some effective techniques in using their meeting templates, carrying agenda notes over between recurring meetings, including collaborators within the agenda, and applying this for other key meetings through the Chrome extension integrating straight inside of Google Calendar.

(It also renders the agenda panel right into Google Meet which is quite handy.)

In any case, follow-ups get the job done once you make them happen.

6. Create a Medium for Async Collaboration

The difference between task-based activities (small, cohesive, time-bound) and long-term strategies is vast.

Setting up an 8-hour strategy meeting is rarely effective (and hardly possible for your entire management team). And it’s virtually impossible to cover all high-level points efficiently within an hour or two.

Therefore, setting up a separate space for asynchronous discussions and conversations is an effective way to leverage everyone’s thinking process with fewer time constraints.

Strategic discussions are contingent on context. There’s a continuous feedback loop. Day-to-day conversations may influence that, and provide an enriched mix of examples and use cases to tackle.

We looked into a number of async tools that provide the best mix between IM like Slack, email, and document management software while being simple and minimalist enough to avoid distractions. Some examples are Twist, ReDesk, Notion, Threads, Carrot.

Some of us use Notion for other activities and are familiar with the editing experience, but in terms of assignments/reminders, it isn’t quite tailored to this. Carrot wasn’t quite stable, and we’ve tested Twist previously—it ranked second on the list.

So we moved to Threads.

The UI resembles email (and management historically spends a lot of time in emails back and forth.)

It allows you to set high-level folders for the main topics (management, strategy, HR, product, vision, etc.) and start asynchronous threads for everyone to chime in. You can request feedback from specific people or keep that open for everyone to browse on a regular basis (harder to enforce).

Notifications and reminders work well, and so do integrations with Slack and other tools in use.

7. Provide Internal Coaching and Feedback

Promoting internally is a great strategy for retaining your best people and empowering them to carry the vision forward.

However, the lack of background in leadership and team development means a limited perspective into high-level management strategies and techniques, popular startup and enterprise frameworks, and established leadership models that larger organizations use.

In order to teach the best practices, you need to:

  • Keep yourself up to date and invest in your own education
  • Work with consultants, advisors, coaches who will push your management skills further
  • Employ training courses and advisory sessions that your team can learn from

This is an ongoing process and you can start with the internal processes you want to establish now.

Once you identify the main goals for the first quarter or two, ask yourself: what qualities would be most beneficial for your team to pick up to perform better?

Then, follow the framework above and execute.

8. Invest in Training

Expanding further, training will be beneficial for everyone on your leadership team.

There are plenty of areas you can focus on personally to move the needle:

  • Speak with other executives and managers in your close network. Ask them how they approach internal training and education.
  • Look for established management training firms or consultants specializing in this. While certification may not be important for the business, the training models may be instrumental in bringing everyone to the same level.
  • Books. Tons of books for leadership development are available out there. Purchase copies for your management team. You can start a “book club” with one book a month that everyone has to read to improve.
  • Book recaps. There are services like Summaries, 4 Minute Books, Blinkist that both you AND your management team can use to gather the essence from the best management and strategy books out there.

Discuss the best way to start with your team. Podcasts, video courses, audiobooks may be the best mediums forward. You can gather together twice a month and learn together, or you can present in the form of internal workshops. As this requires a lot of time, business advisors and training firms can help a lot in developing these practices.

9. Help With Hiring

Regardless of whether you are hiring actively or filling in for people who quit recently, recruitment is an ongoing process for every organization.

By establishing new processes and leadership practices, you challenge everyone’s perception of management. Doubt and uncertainty are inevitable as the vision gets clearer and previous working practices are being questioned.

Proactively help everyone with the hiring process. I’ve covered this in multiple recruitment guides here so leverage the know-how and work on refining the job descriptions, your interview process, and your own participation there.

The company culture has to be aligned with the long-term vision. Make sure you proactively participate in the process until everyone is clear on the required traits that new talent needs to embody.

10. Continuously Improve

If you have successfully created your own business leadership roadmap and employed a long-term strategy for your management team, congratulations! It’s a great step forward.

And during the training and self-exploratory process, you will probably uncover new ways to improve your process further and develop leaders better.

I first spoke about EOS (the Entrepreneurial Operating System) back in 2019, and I see that some of our clients are incorporating the blueprint over time. Traction was the book that introduced me to the strategy – and there’s a lot you can incorporate internally (or adapt to your own processes).

Another great leadership primer is Sociocracy. It’s a brilliant read for startups and progressive organizations eager to empower their teams and instill a self-driven model with more autonomy in place.

I’ve covered other management practices publicly available, including my Radical Candor piece for Entrepreneur.

Keep investing in training and your own education—what works now may be substituted in a year from now through other leadership models invented and refined by progressive organizations.

The Cascading Effect

The best thing about investing in your leadership team is the “cascading effect.”

Once everyone is convinced in the power of strategic planning, this confidence—and efficiency—will be brought to their own teams. New leaders will emerge given enough autonomy by understanding what pushes the business forward.

Intrapreneurs exist and I’m sharing the internal framework for employees eager to grow within the organization

Setting the vision straight—and providing the right KPIs to success—will raise new leaders from your recent hires.

Building a sustainable organization isn’t easy, but having discovered great talent at management positions already, empowering them is the last step of the process. Prioritize the aforementioned initiatives for leadership development and focus on the results.

Your thoughts?