Perry Maddox shares how to identify a struggling leader from afar and explores what it means for us all as leaders at all levels.


“On the left side of your notebook, write down all the reasons you might fail.”

I like to run an exercise with new directors at Restless Development.  

These leaders are among the most important hires we make. They lead a range of diverse, dynamic teams around the world.  We hire on potential, not on years of experience, so most are first-time directors.  They’re stepping up and taking on their biggest leadership role to date.

I ask them to open a notebook. On the left page now, 

What might sink you as a leader? 

This Matters More than Any Technical Skill.

We all worry about the areas where we feel weaker or less experienced.   

I know how it feels as a struggling leader. Every job I’ve had came with plenty challenge in it, most of all my current role. Often the youngest CEO in the room, I still need to lead a complex global agency, well. I’m keenly aware that I must perform as a leader while I’m still learning to lead. I suspect it’s the same with many leaders out there. 

There is always lots to learn when we take on new roles or new teams, stepping up as leaders.  Stretch is where the growth is, but a leader’s learning curve is steep and unforgiving.  The cost of leadership failure is huge. Get it wrong and we might sink the ship.

No wonder that we focus on what we don’t know, the skills we want to learn, and the experience we lack.  Our left page fills up. 

Down the page goes the predictable list.

Fundraising.  

Finance. 

Human resources.

The things we’re afraid of. The areas where we feel weakest. You name it. 

Once our new directors have exhausted their list of worries on the left, I ask them to write one sentence on the right side.

“We don’t hear from you.”

The Red Flag that Signals a Struggling Leader. 

Nobody leads well from day one.

Immediate excellence isn’t expected. I don’t even think it is desirable.  I want leaders to grow with the role.  When they grow, they’re also more likely to grow others around them and to grow the impact of our work. A growing leader, done right, is good for everyone.  

So if we’re all growing and taking on a challenge as new leaders, is it finance or fundraising that should worry us most?  Most of us worry about the money first, but having observed many leaders fail over the years, the pattern is universal:

Silence is the red flag.

When a leader reaches out to ask for help, to ask a question, to raise an issue, or to just say hello, we get a sense of how they’re doing.  Then we can better target our support and resources to help them succeed.

If not, we must guess.  Of course communication is a two-way street, but with leaders who aren’t inclined to communicate, it is easier to miss a problem below the surface. Too often new leaders fear sharing that they’re struggling. But if we don’t hear from them, we can’t help. The relationship doesn’t grow, nor does the trust.  In the end, we fall back on systems to manage performance rather than connecting to grow together. 

It’s never long before we lose that struggling leader.

Let Us Know How You’re Doing.

We all struggle at times, and we’re most vulnerable early on. 

I know the feeling. Another leader taught me this exercise when I was taking on a new role with loads to learn.  

What I’m looking for from leaders is communication.  Leaders who value regular connection. Leaders with the self-awareness to ask for help. They thrive.

It is tempting to avoid raising concerns early on. Sadly, not all work cultures or bosses welcome it.  Of course context matters, but those kinds of cultures and views are part of what we’re trying to change.   Gauge your audience for appetite, but never go silent.

Let us know how you’re doing.  Leaders are people. We all go through ups and downs. We are all learning as we lead.  None of us are finished products, I hope.  

So reach out and say hi.  

Ask for help when you need it.  We can better target our support to help you where you want it. Give us a warning on emerging problems so we can help you solve them before it gets bad. Share your successes and ideas.  It’s good to celebrate and to inspire each other.

Don’t be a stranger.  I bet we can help with whatever is on your mind.  

Even if it’s fundraising or finance.

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Author

Founder of Just Open Leaders and passionate about helping other leaders to create change in this world.

10 Comments

  1. can’t agree more, it is difficult to share our vulnerabilities (areas to learn) and once we start sharing then we learn. we become successful and are in a better place .

    • Perry Maddox Reply

      It’s one of those funny little things that’s so counterintuitive, but sharing vulnerabilities is one of the best ways to build strengths isn’t it? Glad you like this one!

  2. Hi Perry,

    Great post, I recognize much in what you write. Communication is key, being visible in good and especially troubling times.

    I see another opportunity in openly reflecting on your own vulnerabilities, character and skill set. Not only you can set a personal path of growth, but it is also the first step in surrounding yourself with people that are complementary. They will make you a better leader and vice versa!

    Keep up the good work,
    Floor

    • Perry Maddox Reply

      Thank you Floor,
      You’re spot on in the opportunity that comes from embracing our vulnerabilities. That notion of surrounding ourselves with complementary people is one of the best leadership approaches out there in my belief. We spend far too much time worrying about building up our weak areas, when it’s so effective to staff them with complementary people and to let everyone focus on building strengths.

      Congrats on your coming launch and thank you for your kind words here,

      Perry

    • Perry Maddox Reply

      Thank you for the kind words Princess! I hope you are most well these days and thanks for this feedback to help me continue to shape Just Open Leaders to be as helpful as it can be! Please do let me know if there are topics or issues you’d like me to explore in the blog in the future.

  3. “We hire on potential, not on years of experience” I wish this will be the approach of other organizations to hiring young people who have so much potential but lack of experience.

    I love the focus on communication and asking for help. My most productive moments were when I accepted my shortcomings and asked for help; it always leads to a better outcome.

    • Perry Maddox Reply

      So true. I wonder if other sectors have more success hiring on potential than others? I mean it should be obvious that an organisation like Restless would hire young on potential, but then again many youth orgs don’t. I wonder if the tech and startup sector has more experience here? Of all the business I would guess them, but no idea if that’s true.

      Love your reflections on productive moments. I was thinking just today that many of most productive conversations with my bosses or boards have come when I asked for help. As you say, it’s a great way to a better outcome.

  4. Sibulele Mgugudo Reply

    Perry I wish many companies or youth orgs would believe in young people that are non experienced but are eagar to learn and are willing to grow with the company like my self. In South Africa in the Eastern Cape where i stay there’s a huge unemployment rate due to what other companies are doing other companies want experience other companies it goes by who you know in HR department or in management. Which I believe that is unfair, other youth members turn to drugs to alleviate the pressure of not working others get in deep depression wanting to take the life away, thats why we are experiencing alo’t of unwanted pregnancy and high crime rate committed by the young people.

    • Perry Maddox Reply

      I wish the same. Youth unemployment is one of the biggest crises in our world today, yet few want to talk about it. I know it’s even more challenging in the Eastern Cape and that such widespread unemployment contributes to far wider social problems as you say. I wish more companies would see the benefit of age diversity in their workforce, as cross-generational working offers a great deal of benefit and might encourage more hiring on potential rather than on connections.

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