A Deliberately Developmental Experiment

When the founders at Upside approached me to develop a business-wide coaching programme, they were clear they wanted to do something different. It felt appropriate that a scaling company that puts talent and the development of talent at the heart of its organisation should embrace a new approach to developing its people. Fascinated by how we can build organisations and develop individuals for the future, and already drawing on Robert Kegan and colleagues’ work on adult development in my coaching practice, I introduced them to the concept of the Deliberately Developmental Organization (DDO).

This article unpacks how we developed a deliberately developmental coaching programme for Upside, and what we’ve learnt so far along the way. If you’re a leader in a high-growth startup who wants to know how to embed a deliberately developmental culture in your business, or if you’re interested in DDOs generally and would like to learn more about them through a real life example, then join us on this journey of discovery.

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What is a Deliberately Developmental Organization?

A DDO is organized around the deceptively simple but radical conviction that organizations will best prosper when they are deeply aligned with people’s strongest motive, which is to grow. Deep alignment, it turns out, requires something more than making “a big commitment to our people’s growth,” admirable as that may be, even when such a commitment is followed up with significant investments in people’s ongoing learning on the job. It means something more than consigning “people development” to punctuated moments outside the flow of day-to-day work, such as standapart trainings, high-potential leadership development programs, executive coaching, corporate universities, or once-a-year retreats. Deep alignment with people’s motive to grow means fashioning an organizational culture in which support to people’s ongoing development is woven into the daily fabric of working life, visible in the company’s regular operations, dayto-day routines, and conversations.

The Deliberately Developmental Organization

“Culture eats strategy for breakfast” is a polarised way of thinking. Instead of taking an either/or approach, DDOs adopt a both/and mindset to fuse “culture as strategy”. In this deliberately developmental experiment we set out to use the coaching programme as a means to bring members of the cohort, and in time everybody across the organisation, into an ongoing developmental journey in the course of working every day.

A Deliberately Developmental Experiment

Getting started

Customer development interviews were carried out with the founders and a cross section of the team to test the hypothesis for the programme and inform its design. Here’s what we landed on for the programme:

As Upside grows as a business, our people need the right support to grow too. That’s why we’re launching the Up! coaching programme, an experimental but committed approach towards developing the whole Upside team in a way that aligns with our core people and talent values.

Seven people joined the first cohort which ran between July and November 2021. They experienced a combination of:

  • One-on-one coaching – matched with their own professional coach, each participant had six one-to-one coaching sessions over the duration of the programme. Sessions were virtual, each lasting one hour.
  • Group Circles – running concurrently with the individual coaching sessions we ran a series of three facilitated group Circles, held at the beginning, middle and end of the programme. These were an opportunity to share openly what participants were learning and discovering about themselves through the programme, continue to build psychological safety, feedback on the coaching program itself, and embed Deliberately Developmental Organization principles across the business.
Deliberately Developmental Organization - Coaching Programme Timeline

If the programme was the success that we hoped it would be, the intention was to run a second cohort beginning at the start of 2022. In time, the ambition was for every person to experience the programme. From the start, we were also thinking about how best to open up the learning from the first cohort’s members to the whole team, the potential for peer support groups, and how to continue to embed a coaching culture across the business. More on that later!

Design principles

  • Complement, not replace Upside’s existing coaching and mentoring work – Upside was already committed to developing a coaching culture amongst its people, in terms of their day-to-day interactions (we’ve since delivered further Introduction to Coaching & Mentoring training to the whole team to help embed these skills). The programme brought in professional external coaches to help participants develop more deeply as managers and leaders, and have a private space to think things through, beyond more tactical, day-to-day activities. 
  • Genuinely innovative from a people and talent development perspective and transformational for participants “as we grow, this will grow with us” commented one employee. From the outset, we took an experimental approach to this programme and potential future iterations. We knew we wouldn’t get it right the first time, so we went into it with a curious, open mind and a feedback heavy approach (see public links to unredacted feedback below).
  • Cohorts would be made up of individuals from all levels across the business – embedded in the design from the start was the principle that everyone should experience development across the business. Read more on why we consider this to be so important to creating a Deliberately Developmental Organization below.
  • Heat moments – like a hard yoga pose, or lifting weights in the gym, we develop most when we are stretched outside our comfort zone. When it comes to developing talent in startup and high-growth companies, evidence suggests that: “heat experiences are the fuel of development for all leaders, but this is particularly true in tech where employees are smart, hungry, and learning agile”. What’s also needed is a supportive ecosystem in which to experience these ‘heat’ moments, or else a business risks lurching too far to the side of burnout. This balance of accelerated development and support was exactly what we wanted to facilitate through the coaching Circles. We stressed to participants that some of the exercises and conversations that would take place wouldn’t necessarily be easy, but they would help them see and experience themselves and others in new ways.
  • Voluntary, not mandatory – executive coach Ed Batista writes in Getting Coaching For Your Team that “while in some circumstances it may feel tempting to make coaching mandatory, such an approach will likely undermine the process and may doom it to failure. An employee who feels required to work with a coach will be slow to develop a sense of trust and may never be willing to speak candidly”. Participation in the programme was in no way mandatory. All participants were given a clear choice about whether to participate and no negative judgment was made if they chose not to.
  • Confidential coach/coachee conversations – whilst this should go without saying, it’s good to emphasise. Upside were happy that, operating within their own agreed ethical boundaries, coaches could discuss emerging themes outside of sessions and feed these back as appropriate.
  • No association with performance management – the cohort would be a ‘safe space’ for personal and team development. There would be absolutely no interaction between the programme and the business’s broader performance framework and cycle.
  • Feedback rich but quantitively light“not everything that counts can be counted, and not everything that can be counted counts”, said Albert Einstein. In a world obsessed with data and measurement, we think Einstein had a point, particularly when it comes to human beings! Quantifying outcomes in human development is a contentious subject. As you’ll discover below, for this first cohort, we sought extensive feedback but resisted the urge, at this stage, to capture it in rigid quantitative form. How we collect feedback and measure success is something we’re keeping under close review.
  • The right coaches for the job – we needed a team of coaches that were excellent coaches in their own right, but who also understood the dynamics of working a high-growth, startup environment. Collective was born, a hand-picked group of coaches, mentors, leadership professionals and founders, who bring their wealth of experience to the high-growth space.

How was the coaching programme Deliberately Developmental?

Upside does not identify as a Deliberately Developmental Organization in the way that some companies do: think of this programme as being ‘DDO-lite’. But here’s some deliberately developmental themes that have become core to the programme:

One Big Thing

In the first Circle we split participants into pairs and asked them to coach one another on three things that they’d like to work on. We framed this as ‘things to work on’ as opposed to challenges, issues or such like. 

Without biasing them to the concept beforehand, we then introduced participants to the idea of focusing on One Big Thing. We borrowed this from Kegan and Lahey’s Immunity To Change work, in which they encourage executives to identify a single goal “that would excite you personally if you were able to make big gains on this goal”.

From the three ‘things to work on’ already identified, people went back into pairs and helped one another identify their One Big Thing. The questions below were shared to help them double down on it. Participants were encouraged not to pick something technical, that they could accomplish by learning a new skill. Rather it should involve growth as a person. They were also strongly encouraged not to dismiss the other things they’d identified they wanted to work on. They would have the time with their coach to explore these further. We just wanted participants to identify the most important aspect of their development and bring it to the group.

Deliberately Developmental Organization - One Big Thing

Participant’s One Big Thing were revisited in the second Circle. We spent almost an hour going around the group, asking participants to stand up and share their reflections on their OBT encouraged by the questions below. Everyone else sensitively probed and shared their own thoughts and perspectives on each others One Big Thing. 

Deliberately Developmental Organization - One Big Thing

Reflection: having an OBT helps an individual focus on a specific area of their own development, beyond just the acquisition of new skills. But it does much more than that. Imagine a culture in which everyone in your team, and the business more widely, knows the core area in which you are seeking to develop. Everyone around you can help you move towards it. Further imagine that you are the CEO and everyone in your business knows what your core development goal is. What would that feel like? Rather than this being something shared only with your Board, executive coach and a few close senior others, anyone in the business can give you feedback and advice on the progress you are making.

A whole-company approach

The traditional talent management approach is for organizations to identify a relatively few “high potentials” and “business-critical” leaders and provide them with individual coaching, off-site workshops, leadership development programs, and other special experiences outside the normal flow of work. The theory of this approach is that people will bring what they’ve learned back to the workplace—but the reality is that the learning often doesn’t transfer or take hold when carried back to one’s work setting. Traditional approaches are for too few, applied too infrequently, and go on too far away from the real work. In contrast, “an everyone culture” treats all members of the organization as high potential and designs the work environment so that development happens in the regular course of work for everyone, every day.

5 Questions With Robert Kegan, Lisa Lahey And Andy Fleming On ‘An Everyone Culture’

The programme blended personal, one-on-one coaching with group, coach-approach Circles. From Upside’s co-founder and Director of Talent, through to the least experienced members of the team and newer hires, the first cohort was made up of individuals from across the business.

Why were we so passionate about this blended approach, and that the cohort was made up from what Kegan and his colleagues call a “diagonal slice group”?

  • We’re all works in progress – none of us have it all worked out and we can all be better managers and leaders. To truly democratize coaching, everyone should experience it across the business. It shouldn’t be the preserve of the leadership team, neither should Individual Contributor / manager-level development be striated and detached from those at the top.
  • Empathy and perspective taking are vital skills in a complex world – by hearing and seeking to understand the emotions and perspectives of both their junior and senior colleagues everyone across an organisation becomes better connected. From senior through to junior, and vice versa, everyone experiences their colleagues in a more human, vulnerable and authentic way.
  • Psychological safety – on a compounding basis, the approach encourages the development of a psychological safety, an established leading indicator of happy and successful teams.

Reflection: the most powerful moment of the whole programme for me was when Dave McGahey openly shared amongst the group the challenges that he was facing on his evolving leadership journey, including an acknowledged shift from seeking development “tools and frameworks”, to a deeper exploration of “purpose and identity” and questioning “what do I want to be?” 

Supporting a Deliberately Developmental Ecosystem

How much do you know about the inside workings of most management and leadership development programmes? We think the answer to that question is ‘not much’. Leadership development companies want you to read their thought leadership and testimonials. Companies want to extol the virtues of developing their people. But when it comes to sharing details about what methodologies are being used and, crucially, what participants are actually saying about their developmental experiences, little is shared.

That’s why, for the first Cohort, we took a very deliberate (excuse the pun) decision to Build In Public. You can see exactly what approach and methodologies we used for the programme by visiting the dedicated Notion page (login may be required). You can also read participant’s feedback from the First and Second Coaching Circles. Here’s a few selected quotes, but check out all the feedback via the links so that you know we aren’t just cherry picking the best ones.

It is central to the success of my direction and energy at present.

Circle 1 participant on identifying their One Big Thing:

Everyone was really open, very little went unsaid and you could tell people were being frank. This surprised me as, despite being a small company, I haven’t worked with all of the group members closely and so this willingness to really share what they feel their weaknesses are or what they see as improvement areas was fascinating and the team definitely feel closer because of it.

Circle 2 participant on the overall experience of the session

Reflection: ‘open-sourcing’ this programme felt liberating. We hope it contributes to the range of resources out there on Deliberately Developmental Organizations. If nothing else, we hope it might give you some inspiration about how you can grow your people in your own organisation in a deliberately developmental way. 

An experimental, emergent approach

Followers of Kegan and his colleagues’ work will know that it’s rooted in the theory of Adult Development. Research into adult development shows that, over time, the way humans construct reality can become more expansive, less distorted, less egocentric, and less reactive over time. This is rooted in our expanding capacity to handle increasing levels of complexity.

In that vein, we embraced a complexity mindset in designing and delivering this programme. It was impossible to know in advance how this programme would land with the team at Upside, nor what it might grow into. So we went into this with Upside in an experimental, iterative and emergent way.

Reflection: perhaps one of the greatest contributors to the success so far of this programme has been the willingness of Upside to experiment with us. My coaching colleagues and I do this work for a living, we’re deeply passionate and we know our stuff, but in a complex world no one can have all the answers or know what the outcomes will be in advance. We’re fascinated to see where this work takes Upside and us, as coaches.

A Deliberately Developmental Journey

And so our experiment is evolving into a journey. We kicked off Cohort 2 in February 2022 with another 8 participants, with the ambition to roll out another cohort after that. We’re taking all the rich learnings from Cohort 1 and applying them to Cohort 2, whilst introducing and testing new ideas along the way. We’re also thinking about how to embed developmental principles across the business, through ongoing cohort catch ups and focused coaching, management and leadership training. 

Deliberately Developmental Organization - Example

We invite you to join us on this journey, as we wrap more structure around the programme, whilst remaining open and adaptive to changing it based on what we learn. Sign up to my monthly leadership newsletter for further updates and follow me on LinkedIn and Twitter. You can follow Upside on LinkedIn too. We’ll continue to share our learnings and celebrate our deliberately developmental successes (and failures) as we go!