When I became a boss about 14 years ago, no one told me what to expect. I was not told a lot about what was expected from me either. I tried to meet all of my perceived expectations, and failed. I wasn’t a bad boss—my people loved working with me and we created a great product. I had bent myself into a role and I just didn’t feel good. I avoided conflicts and difficult conversations. I didn’t know how to get the best from me or my people. I didn’t dare to ask for help, as I was the boss.

Read more stories of bosses I’ve worked with that may resonate with you.

Lonely At The Top

Lonely At The Top by Harsha K R

Now you (or a boss you know) can get help in a gentle, trusting way. You will have a caring peer around you all day to help you see what is happening in your interactions. We will reflect on conversations to build a new awareness (like entering the Matrix). I will help you see your reality in a new way, enabling you to identify new choices.

Top Reasons To Ask For Boss-Pairing

  1. You don’t want to be called the boss.

  2. You feel you’re too involved in day-to-day business and want to be free.

  3. You trust your people, but they don’t feel trusted.

  4. You want to make changes in your organisation with less resistance.

  5. You need help dealing with emotionally difficult situations.

  6. You want to again love what you do and be loved for how you do it.

What Am I Offering To You?

I trust you to be able to be a leader who’s loved for the way you lead.
I see the good in every human being and acknowledge the good things you do.
I increase your self-trust and confidence.
I offer empathy for your feelings and the feelings of those you communication with.
I offer non-violent ways to navigate and resolve conflict.
I give you my perspective on challenges you’re facing and help you discover new options.

In many organisations, being or becoming the boss requires to cope with judgement and competition. It bears the risk of giving up our authenticity for success. Our need to be acknowledged may override our need to be ourselves. We don’t feel safe. We lose trust.

I create a container of trust at the top.

What will happen?

We will have a one hour setup call in advance.

You will need to reserve a full day with me including 2 hours of one-on-one time together at the end. At the start we’ll make an agreement on how we pair. Maybe you’re aware of specific challenges you want help with. Maybe you are curious to get a second perspective. There are different options for how we spend our time – we can do an all-day Temenos or coaching if you want. A good way to start is for me to shadow you all day in your regular schedule.

Afterwards we’ll reflect and learn. You may appreciate my presence and want more of it.
You may want to continue boss-pairing or ask me to work with your leadership team.
You may identify other initiatives in your organisation you want help with.

What Other Bosses Say

“Olaf is a constant source of useful oberservations, feedback and inspiration” – Alexander Kranki, Krankikom GmbH

“Olaf talked to everyone at eye level, which was the foundation for our trustful collaboration with him.” – Christian Beck, MeVis Medical Solutions AG

“Olaf is an excellent speaker and inspirational thinker who understands that respecting people is everything. If your organization needs to refine its way of working, become lean and think out-of-the-box, then call him.” – Sampo Hämäläinen, VP Europe, Futurice Group

How Is This Different From Executive Coaching?


  • Co-aching: support focused on the “I don’t dare to” kind of issue

  • Support from the heart

  • Focus on authentic and open communication

  • Agile mindset, cultural focus, transforming our reality through stories

I Am Special

  • I think in systems: Leverage for transformation at the top, where it’s most needed.

  • I work explicitly with trust to increase confidence, and love.

I Understand You.

I Understand You.

How to get started

Contact me. Make an appointment using the button below.

Email: Olaf AT Lewitz.net.

Connect on Xing. LinkedIn.

Tweet me.



  1. Olaf Lewitz Boss Suffering Stories » Olaf Lewitz
    January 31, 2014

    […] 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. […]

  2. Jake Calabrese
    February 3, 2014

    Olaf, I love the idea and the concept of helping leaders with boss pairing! While I know this will be an edge for many leaders to even consider – the ones who choose to do this will be blown away by the insights and perspective they uncover! For me, reading this post, I am again wowed by the container you created and courage to simply state what is real, all in a ‘simple’ blog post. Inspirational!

    • Olaf
      February 3, 2014

      Thank you.
      Glad you like it:-)

  3. Olaf Lewitz De-Scaling Inspirations » Olaf Lewitz
    July 31, 2014

    […] Boss-Pairing […]


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