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Practical leadership development tips from PI’s President

Last week, we talked about leadership capacity—why it’s important, how to measure it, and four core competencies that are imperative for leaders at all levels to learn.

In this blog, we’re going to unpack common questions around implementing leadership development programs and potential sticking points. (And here’s a leadership rubric you can use to help develop your employees.)

How to make leadership development a priority

We know that leadership development is important, but how do you make it a priority—especially in smaller or flatter organizations?

The short answer

The short answer is you have to make time for it, and you have to talk about it all the time.

The long answer

The longer answer is this: Sometimes we create our own blockers to leader development. As a current or aspiring leader, you need to be honest with yourself about what it means to be a great leader. You need a formal way of measuring what good leadership is so you can manage against that, rather than your own self-defined concept. It can be scary to put a formal process into place because you have to look in the mirror. You have to acknowledge that while you may be a good leader, there’s still some work to be done to be a great leader.

Creating self-awareness about your own feelings about personal development will play a key part in rolling out a leadership development program in your organization.

Jackie presenting

Great opportunities to talk about leadership development

There are two annual opportunities I’ve used for the last 15 years to talk about building leadership skills and capacity.

1. Annual exec offsite

Every year we host an executive offsite. Anywhere between 25%–50% of the material we cover is dedicated to advancing talent and leadership. Put a couple of 2-hour blocks on the calendar with senior leaders, and it’s amazing how much progress you’ll make. There’s so much that goes into leadership—you won’t run out of things to talk about!

2. Annual talent audit

To ensure we’re setting and maintaining a high standard for excellence, we schedule a talent audit at least once a year.

Most of us are so busy that if we leave things to chance, they’ll never happen. But if you put it on your calendar, you increase the likelihood that it will happen. Don’t allow yourself to get sucked into the urgent activities of the day to day. Instead, make time to fix the foundational engine of your organization: your leadership.

The right pace for leadership development

Another common question related to leadership development is, “What’s the right pace?” Put another way: “How soon should we start training up leaders?”

My answer is: Go as fast as you possibly can. There is no better time than the present to train up future leaders. The mistake many organizations make is they wait until a promotion is available or someone shows high potential to start training a new leader, when they should’ve started training from the time they walked in the door.

As your business grows, you’re going to need more leaders—of all kinds. Here at PI, we have a saying: Leaders at all levels. Leaders are not just managers. Individual contributors who lead by example or who take ownership of their projects are leaders too. We want to instill leadership qualities in everyone who walks through our doors—not just those who want to ascend the org chart.

While some regulated industries might make it more difficult to ascend in leadership or limit growth opportunities, that can’t be an excuse for not moving quickly or not investing in your people. When it comes to the pace of your leadership development, it’s more about mindset than industry.

A note on leadership development in flat organizations

While startups and flat organizations may approach leadership development differently than larger, more established businesses, the idea of building leaders shouldn’t take a back seat.

When you look at the four core leadership competencies we talked about, you need more of them in these kinds of work environments. Leading a flat, fast-paced organization is a balancing act between chaos and speed—Pareto’s frontier in the startup or flat org context. Strong leaders can help strike the right balance.

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A simple way to develop leaders

There’s no better way to learn than on the job. The key is to help your employees find a way to do it without damaging their personal reputation or psychological safety.

For example: Let’s assume someone on your team wants to learn to be a better leader, and there’s a meeting coming up. Ask them, “What are you thinking of saying? What’s your contribution?” Allow them to think through what they might like to say and prepare for the meeting, then set them up to share those insights (e.g., “Drew, what do you think?”).

These sorts of leadership development efforts will go a long way in not only growing leadership capacity but increasing confidence as well.

How to handle tough conversations with leaders

Tough conversations are … well, tough. But they’re also a critical component of leadership. Good leaders love getting good feedback because it’s the only path to mastery.

That said, there are some ways we can improve the feedback process.

Show them you care.

If your people know you really care about them, it’s much easier to give feedback. Building rapport happens before the feedback session, and it happens through action. How are you showing your people you care?

Along the same lines, be aware of your intent when giving feedback. Great leaders give great pointed feedback from a place of love.

Be specific in your feedback.

It takes courage and caring to give tough, honest feedback. Giving unactionable platitudes or indirect hints is so much easier! Specificity will improve the likelihood that you get the results you’re looking for, and your employees will respect you for your willingness to be honest.

Be their champion.

Your job as a leader is to understand what your people want their ideal resume to look like. Not everybody is gaming for CEO—and not everybody needs to attend business school to be a business leader.

As a manager or HR professional, pay attention to what your employees’ dreams are and help make those dreams come true. Meet with them regularly to work on goal setting, career pathing, and creating opportunities for them to learn and grow.

Leadership development is an ongoing process. By developing leaders at all levels, your organization will start to see the true benefits of talent optimization: better teams, better performance, and better results.


Daniel is the president at PI. He's had fun life experiences—from witch doctors to angry gorillas—in 55 countries!

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