Boss Suffering Stories

Posted by on Jan 31, 2014 in Agile with a Purpose, Coaching, Culture | No Comments

Depending on the kind of organisation and the way the boss ended up at the top of it, totally different issues may limit their or the organisation’s effectiveness. A founder has different challenges than a CEO who was brought into the company later, and again different from a boss who worked her way up through the hierarchy. The challenge of trusting people, again and again, seems to be universal. Bosses need help. Try boss-pairing with me.

I Understand You.

I Understand You.


“When we still worked all in one room, they made all the decisions themselves. I never interfered, and never bothered, as I trusted them”, says Linda, founder of a company which now has one hundred employees.

“We never made any decision without her”, reports one of her first employees.

Being a founder brings a seniority with it that we instinctively respect, if we belong to that system. Even if that situation never arises, we’ll always believe that Linda will sort things out once we fail.

It’s a systemic truth of that system that it’s her system, and joint awareness and empathy of all is needed to truly make it ours.

Climbed the Ladder

“My department heads spent more than 50% of their time and energy dealing with fear of me”, says Peter, CEO of a 250 people organisation. Most of them were his seniors when he started as a software developer. He knows their flaws as managers. Clarity and leadership brought him to the top. Envy and low confidence now create fear. Will they be able to talk about it?

Externally Installed

“He only manages by numbers”, says Kai, VP Products of a company who was bought by an investor who installed the new CTO, Tim. “He does not understand how we work”, says Martin, Senior Software Architect, about Tim, his new boss.

When external forces install someone in a senior executive function, they have expectations. The staff has expectations too, and they are generally not the same. How do you behave in a situation like this? It’s hard to stay authentic. In most organisations being authentic and honest does not help you to climb the career ladder. Tim and Peter have been repeatedly selected for being and trained to be inauthentic by their work environments. Now they are in a conflicting situation, creating dissonance, and pain, for themselves and others. Will the people involved treat each other with empathy and understanding?

Daring to Trust, Again

Mary, Co-Founder of a 25yo software company: “You always want to be open towards new hires, trust them and invest in them, even if you’ve been disappointed multiple times and felt hurt, personally. We struggled multiple times with situations like this: you find a gifted young employee from university. You teach them all you know. You enjoy their growth. And then they leave, to the big competitor. You know they’re doing the right thing for their career. As a human being, you still feel sad and disappointed. You’re tempted to keep a greater distance in the future.”

These stories are all true, from my own work experience (Names changed, of course). If one of these examples resonates with you, call me. Or send a link to this post to your boss. I’ll help her to again love what she does and be loved for the way she does it. I’ll pair with her to make that possible.


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