Struggle to Succeed Coaching

Coaching, one of the most important skills of leader, is easier said than done. Many leaders experience the fear of being wrong, making mistakes or completely failing. Such pressure results in leaders being more directive, such as what to do and where the answer is. Although it’s more time consuming and invites additional risk, I push my direct reports and new leaders to struggle to succeed, the idea that encourages direct reports to struggle with a challenge in order to reach beyond what they think is possible.

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Components of Coaching

Earlier last year, we rolled out our empowering leadership style at cleverbridge. A key principle required to act in an empowered way is to be a coach to your employees. But what exactly does coaching mean and how is it different than mentoring?

There is a huge difference between teaching someone and helping them to learn. In coaching, fundamentally, the coach is helping the individual to improve their own performance: in other words, helping them to learn. Mentoring is a type of coaching that relies heavily on share experiences.

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Different ways to Coach an employee — Not all Equal!

It’s easy to fall into the trap of telling people how to do something. A direct report comes to you with a question and you simply answer the question with advice on what to do or worse, tells the person what steps to take. As a leader, you have helped your direct report get to the right answer, but does giving too much direction or the answer help the person next time they face a hurdle? Or is it better to act as a sounding board for their ideas or even use questions and challenges to help them? I advocate for the painful step of letting them struggle.

I remember in the earliest days of cleverbridge with 3 full timers and 4 part timers where I employed this model out of necessity. We were growing fast and I didn’t have unlimited time to spend with those earliest employees, so I gave them some basic training and told them to try and figure out problems on their own first. But I offered an important caveat: bring their solution to me and I would review it. This allowed those earliest employees to struggle on their own for a while, but never be put in a position to fail. It was a win-win and I saw their rapid growth in those early days. This built trust and loyalty that remains to this day.

When I started restoring vintage stereos, I didn’t know how to read an electronics schematic. Fortunately, I had mentors and coaches all over the internet who provided advice, but also asked questions to help me learn. I struggled quite a bit to understand the terminology, read the schematics and apply that knowledge to what I was seeing. However, I’ll never forget the sense of accomplishment that I felt the first time I plugged everything in and the stereo played sound. It was probably Q101 in Chicago playing Oasis or R.E.M.

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Vintage Stereo and TV Schematic

My experience is that it takes self-control to give advice, not the answer. It takes self-confidence to add risk when not necessary. And it takes a coach to see the long-term benefit over the short term cost. I firmly believe in encouraging my employees to struggle to succeed.

Global flexible billing entrepreneur of @cleverbridge with a passion for recurring payments and customer experience. @hydeparkangels board

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