Lessons on facilitating systems-level conversations

What does it take to get common alignment with multiple-level stakeholders?

As a newly-minted social designer (graduating from my MFA in Design for Social Innovation), being back at work as a designer in government has given me a fresh set of eyes and perspectives — around what it means to facilitate system-level, cross-sector change.

Our team is tackling food insecurity in Singapore, as part of a multi-agency workgroup in the food support sector. We bring together government agencies, charities and community groups, to enable better coordination and more choice-enabled food support.

Having facilitated my first workgroup session with multi-level stakeholders (back in July 2021), here are some lessons and emerging questions!

Image inspiration Ingrid Ma

Keep people grounded in shared purpose and the WHY

“Aligning on why is more important than aligning on how.”
— Julie Zhuo

Differentiate in a particular moment, whether the conversation that is needed is one of action or intention¹.

In a separate conversation with community groups supporting migrant workers — we started the conversation with, “What was the injustice that brought you here²?”. It was amazing to witness the connection that community leaders formed with each other, through the stories they shared. The conversations flowed in a way that showed how we were all aligned towards a common purpose.

Often in the interest of time, we move straight to doing. When we do that, we get caught up in issues that bring us apart rather than together, and nothing to ground us on why the work matters — to push beyond individual interests and elevate collective goals.

“To deal with the complex sustainability challenges we face, a different kind of awareness is needed; a shift from ego-system awareness to ecosystem awareness.”
— Otto Scharmer


How can we co-create visions of a shared future that each stakeholder can recognise themselves in?

How can we move towards solidarity, as a collective whole?

How can we maintain the spark and excitement in tackling a long-drawn, systems-based issue?

Image reference creativityculturecapital.org

Constantly assess power dynamics and how it shapes the room

This points to two levels of power — the power we bring with us as representatives of our respective organisations, and the power we have in the context of a facilitated conversation, by how much space we take up.

As part of a multi-agency workgroup, each member plays an active role in recognising where power lies and re-distributing it. Without clear intentions, we often default to old patterns, but it doesn’t mean it has to stay this way. Government vs larger charities vs small community groups — power manifests through previous interactions, relationships, and external factors — but a shared space gives us an opportunity to explore new possibilities on how we relate to one another.

As facilitators, we are responsible for sustaining an equitable space.

I’m sure we can all remember that one time where one person ends up speaking 80% of the time. A technique to tackle this is to start with group agreements, to invite the right kind of participation. These shared agreements have to achieve a certain level of resonance, in order to be effective.

Over at Flox Studio based in NYC, they utilise the concept of a ‘Feminist pause’. This preemptively surfaces the likelihood of someone taking up too much space, and an agreement on what happens next — to call it out, and take a pause in service of those with less power. Personally, this is definitely an area of growth, to be able to bring this awareness to the room, and more so to have the courage to call it out when it happens!

If time allows, consider including exercises that bring out individual voices! As much as possible, take care of entry and exit, with simple check-ins/ check-outs, which can even be done through the chatbox.

This unicorn scale of greatness (by Emily Culyer) is a great way to inject some element of lightness, introduce individual voices, and get a vibe check of the space.

🦄 — unicorn greatness
🐊 — strong and snappy
🐘 — strong but with heavy shoulders
🐢 — good but wanting cover
🦔 — tired but going at own pace
🎈 — a little deflated


What does it mean to call out power in a respectful way?

What does it mean to reflect the system back onto itself (e.g. visually reflecting how much time each person has been speaking)?

How can we have honest conversations about power?

Lay the groundwork for the collective work

In a workgroup setting, people want to feel heard, and may enter with their own personal agendas. This leads to the session derailing when seemingly unrelated topics come into play. With messy, ‘unfinished businesses’, the facilitator may end up being pulled in all directions, especially when there isn’t a strong outcome that grounds the discussion at hand.

Before engaging with different stakeholders all at once, they may also have their own opinions to sort out within their organisations.

As much as possible, we seek to address potential trigger areas beforehand and also give space for organisations to build up their own collective understanding and frame of mind. Some methods for addressing this are:

  • Individualised interviews and pre-sessions to ensure voices are heard.
  • Pre-surveys² can also help to bring out points of contention present in the room. Start the session by visualising the responses and helping the system see itself better.
  • Pre-work/ ‘homework’ kits³, which could come in the form of a slide document with question prompts. This also helps to include voices and perspectives of those who might not be able to be present during the session itself and is a potential way to reduce the overall group size.


What is the trust needed for participants to see the value and commit their efforts?

How can we do justice to concerns and opinions raised?

Here are some mini-lessons still percolating:

Have clarity on specific session-based outcomes

We realised quickly in hindsight, it’s not just important to set goals, but also to clearly know what we want out of the session! It’s much more practical to frame discussion points with an understanding and alignment of what success looks like, and what to do with the responses we get.

Be adaptable

Facilitating group level conversations is parallel to being in a flow-like state, being ever-cognizant of the energy level and constant change in dynamics, while having the confidence to adjust the sails, to bring everyone to shore towards the end!

Reflect on the process instead of just action items

It’s easy to dive straight into the ‘what’s next’ after a session. Build a routine for team members to be reflective over the process, not just the outputs. Retrospectives are also a helpful way to gather collective learning over how things went, and whenever possible, it’s also helpful to include feedback from participants as well.

Hope this helps in your next group level facilitation, and feel free to reach out if you’ll like to chat more.

We are also hiring!

[1]: Shoutout to Khai Seng for this nugget of wisdom.

[2]: Credits to this 3-part Reboot Masterclass Series on driving transformative collaboration (highly recommended!).

[3]: Thanks to the OurSG Grants design team (Kanika, Mel, Enrico) for sharing your experiences!



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