Karilen Mays
September 11, 2023
min read
People & Culture

Thoughts on the Challenge of Career Progression & Holacracy

This is the story of Karilen Mays, a writer, advisor, and facilitator who helps individuals and groups. Karilen worked as a Partner for HolacracyOne for 7 years.

What does self-management have to say about career progression and professional development?

The short answer to this question is that Holacracy is silent. Holacracy does not suggest anything in particular. Holacratic companies have to come up with their own answer to this.

For example, the organization could allow all employees to have a training budget for anything they want each year, even if it is a small budget. Or maybe funds are low so the organization does not fund anything unless it is needed for a business value to aid a role, rather than supporting individual desires for growth or the longer-term interests of the team or company.

Most teams will create something somewhere in between. For example, Pariveda Solutions proposes a talent and career development framework that includes:

  • an onboarding training program,
  • a yearly all day employee-run conference,
  • regular learning events and study groups to help employees grow,
  • cross-functional teams that are built to encourage the sharing of knowledge,
  • a social media strategy that focuses on delivering actionable training content.

That’s on top of the formal training programs on how to lead teams, manage your career and work with team dynamics!

Even if your company is not quite mature enough to implement such an extensive framework to support career development, the scenarios I describe are all compatible with self-managed organizations and Holacracy. You could even propose a policy similar to one of the examples above if you need to try something different in your self managed team.

However, just because something is compatible with Holacracy doesn’t mean it works better than in a traditional environment.

My HolacracyOne Experience

Earlier in my career for years, I thought Holacracy would be a good way for people to professionally develop themselves. For me, working in such a dynamic environment with explicit tools increased my capacity for ambiguity and perspective-taking, among other things. Roles and structure also helped mature our business functions.

However, to have these high performing teams for the work of today and attract and retain talented people, we need personal support for growth and learning. While I am still excited for people to develop careers that are workable for them and create more dynamic environments, I think there are some critical aspects that Holacracy either misses or doesn’t address. This article will focus on my first hand experience.

When I worked at HolacracyOne, I felt that professional development and career progression was primarily an individual responsibility. I struggled with it, both personally and on behalf of the organization during and after my time there, as a partner and in many various roles.

There were some changes and improvements over time. An ad hoc approach may be okay for some, but this is not really a case in career progression best practices. This is because as an LLC with no employees, the founders intentionally did not want to have to address 'people' issues, including talent development.

Still, we can apply some takeaways from the challenges of progression to other current situations.

Career Development Tension By Tension

In my case, how would I go from a person who has been trained in facilitation and coaching to doing delivery work, directly helping people?

I had to figure this out.

This was my aspiration. In those days at our small company, there was no formal career path or career development since up until then, two of the founders did the consulting work. I was not a trained consultant, and neither were they.

What was I to do? I had to take initiative and get the help of my colleagues.

Someone had the idea of shadowing some client meetings. This was expensive time-wise for an 'unnecessary' team member to attend. Time or money were often given as objections about why we could not bring an extra person to learn. So I shadowed virtually.

Then when there was a need for a team facilitator, I was willing to try. With about one meeting under my belt, I remember nervously showing up to my first solo client meeting. That was the beginning. Now this was largely made possible by the fact that this was work we needed to do, not everyone wanted to do, and I was motivated to learn.

Jumping Off a Cliff and Building a Parachute on The Way Down

In another scenario, a two-day workshop, a high margin ‘easy sell’ of $10,000 or more was delivered by a single person, but it was a lot to manage. In the workshop, there were facilitation and coaching opportunities.

Now there was a question of how could we bring in less experienced consultants in what seemed like vulnerable situations? We could just simply decide for me to show up and do it.

I really wanted to do well at the work and develop a career path too but it was a lot of pressure. I remember my first client workshop on site. It was in New York. In those days we didn’t prepare much. There was likely a role defined that I would fill. I co-designed with my colleague and my goal was mostly to learn and add what value I could. The whole experience is a blur, but pairing definitely worked. This strategy of pairing or team consulting worked well for me.

Pairing or Team Consulting to Grow Together

For example, in the Washington state Holacracy adoption, where I was the engagement lead, I was also coaching teams through their first experiences of learning about tensions and tactical and governance meetings.

Though I had what felt like little experience myself, I had a colleague who I had not worked with before who played the (Holacracy) secretary role. Presumably, he may have also had less experience. He was able to observe my process and coaching points.

Then in a different team’s first meeting, he led while I played the support role so I could also coach. I think it worked well for both of us to have the team support delivering, and watch and learn as a backup.

It was critical for scaling and professional development to do these things, and to be fair it was also a young company.

Even in a company that 'wrote the book on distributed authority' with skilled practitioners and good intentions, it was still challenging to create meaningful and accessible career development opportunities.

Why Was It So Hard?

One challenge was the various objections like this is not a business need, say for a person to go shadow and team consult. The challenger could point to the membership agreement and say it was an individual responsibility. There was a case of one partner who had been trained as a professional consultant wanted to go take the coach training or attend, if I remember correctly. Keep in mind that our own company created, priced, and delivered the training program.

He had roles and career interests that meant it would be good for him to attend the training. It was obvious (to some of us). I believe it was suggested that not only would the organization not pay for the trip or pay him to do it, but that he could personally do it on his own time, pay the direct event costs, and pay his own expenses. Maybe I had a role that proposed the organization pay his direct event costs or make it due six months in the future.

It felt weird and wrong, but with no formal development program and the stance of no business need, it seemed like the best resolution at the time.

In fact, the membership agreement (like an employment contract) said partners were responsible for their own professional development. The understanding was this was the responsibility of the individual.

While there may have been tax benefits to partners with this document and practice, it severely limited the organization. I think it was a symptom of some partners believing that the people are not any of the organization’s business, but stewards or even servants of the organization.

What Would I Do Differently?

Though I did change the benefits and progression norms as time went on, just as a few others did, I wish I would have challenged the status quo more and advocated to formally support people more. I often found myself working around or outside of our system to help people, which was ironic since that was supposedly the point of Holacracy, to not have to do that.

Still, it felt like the best progression opportunities were available to those of us who knew how to best use Holacracy, which excluded others. Eventually, there was a budget for partners to attend one training per year or something like that. They still had to pay their own way, unless a role had a business case but the event expenses would be covered, and partners essentially did it on the side along with a full workload.

If at all possible, I would recommend instead that you install people development processes and people representative roles early in your organization so people don't have to take personal actions that actually benefit the organization.

Key Takeaways From My Experience

Define what success looks like, and be open to reality being different.

While it is good to have an idea of what you want to do and move toward it, take it one step at a time. Set your expectations for your career change and be prepared to adjust them.

Though I had a long term goal of becoming a consultant and facilitator, I did not know if I would be good at it or if I would like it. I had to be prepared for how it would be once I started trying it. It took the time it took, which depended both on my skill and comfort and the work environment.

Join an organization that has some plan for career development and professional growth for its members.

Talk about it with people in your interview process. It is not enough to do purposeful work or to take the initiative in your career. The organization needs to explicitly value people and their development for individuals to not only stay but to have a chance at thriving.

Spend some time to consider: is what you want even possible in your current environment?

There is no shame in moving on to something else if that is what is best for you as an individual. This also may be challenging, though it is also worth considering. It is okay if we do not stay in one role at one company for our whole work lives.

Ask a mentor for help.

If there is no formal training program, then is there someone who has done what you want to do, or who you see as a strong mentor? Ask them to help you.

Even if the organization does not have formal professional development support or career progression options, if there is a culture of support, innovation, transparency, and well being, there could be an environment conducive to making your changes.

Revolutionize your way of working now!