“Thank Goodness it’s Over?” Why I Keep Planning Team Appreciation Month (Despite the Chaos)
Unpacking the challenges and unexpected joys of building meaningful connections at work
“Thank goodness it’s over.”
A phrase that pretty much punctuates my internal dialogue at the end of planning 55 Minutes’ annual Team Appreciation Month, then again at the end of implementation, and yet again when the cycle repeats.
It’s both (1) an expression of relief from carrying the weight of culture-building within the confines of — let’s face it — a business initiative, and (2) an acknowledgement that there’s undeniable goodness to give thanks for in the process, despite the drudgery of planning.
Many long held traditions, rituals, habits, mastery and might I say, fitness is achieved through this process: Rinse, repeat.
Much like our bodies, the culture of appreciation is a muscle in need of flexing within organisations. For the lack of flexing (often in clumsy, tottering ways), we forgo the benefits that this cultural (nay, human) quality engenders: to make us more grateful for ourselves and/with others.
Appreciation is not just a concept or quality, it’s about experience too.
What is Team Appreciation Month?
For us at 55 Minutes, Team Appreciation Month has become somewhat of that fitness routine, or “company ritual” as our head Wendy Wong would call it. While birthed during the pandemic, it’s not a credit the virus can take, but an intentional choice at cultural shift.
A whole calendar month is set aside, with resources poured in yearly to remind us of the importance of expressing gratitude for the people we call our teammates — with whom we laugh, lament and labour alongside for a good 260 working days (~2,000 hours) per year, give or take.
Be it a remote game of Angel & Mortal, Coffee Roulette in small groups, or an Appreciation Hour on a dedicated Slack channel that serves as a gratitude board, it’s about weaving in opportunities for the team to connect and express to one another (in word, deed and other forms of expression):
I see your gift and contribution, and thank you for sharing that with me.
👇 Some of the things we did, and how you can do them too👇
1️⃣ We turned Appreciation Hour into a virtual gratitude board
Mark your calendars and get ready for a dose of encouragement! That’s an uncomfortable notion for a bunch of introverts. Past attempts left us with an awkwardly empty gratitude board. So we switched things up this year with a more guided approach (you may read more about factors that prevent us from rendering kind words here) by:
▪ Allowing time for preparation (so each team member gets to decide what they are comfortable to share, and how they’d like to express themselves)
▪ Providing prompts (on how they can craft their appreciation messages)
▪ Having a schedule to work by (to avoid the unnecessary guesswork about when one should post their appreciation)
▪ Marking out a time window (to keep people expectant)
Budget: Free
Time: Depends on individual (~ 30 minutes to 3 hours)
You might also need: Scheduled reminders to individuals in case they forget their turn.
What may surprise you: Crafting appreciation takes more time and focused effort than most anticipate, especially for those who are new to doing it. So be flexible if you’re fixing a time window. As a planner I was most anxious about how this activity would turn out, but as a participant I received encouragement I didn’t know I needed.
2️⃣ We organised a Coffee Roulette
The team was divided into groups of three or four people, given a planned afternoon off and some pocket money to hang out without agenda, and without the organisers too. Whether it should revolve around coffee, tea or teh-tarik, it’s up to them to find a menu item that people can connect with, and a suitable time of day to ensure no member is left out due to workload or leave.
Budget: $10/pax
Time: Half day
You might also need: Clear intentions on how you’d like the grouping to be done. For us, we wanted to also take the opportunity for those who don’t work closely together to mingle. If you foresee awkward silence, you may consider equipping them with a handful of conversation starters.
What may surprise you: When it comes to gathering in person, work can crop up, and so can Covid and other contingencies. Be ready to adapt your plans or reschedule.
3️⃣ We ran a game of Angel & Mortal
A remake of the original game, each member was given a $30 budget and a whole month to spy on their “mortal” and come up with personal and tangible ways to show their appreciation. From a home-cooked meal delivered to your doorstep to a thoughtfully assembled care pack, appreciation knows no bounds. This one’s great for remote working.
Budget: $30/person
Time: Depends on individual (from 30 minutes)
You might also need: An app to facilitate the randomisation, and a conscious attempt to stay anonymous. Keep the claim process as simple as possible too.
What may surprise you: How much we can learn about our teammates by observation, and the creative things we can do to show our appreciation.
From the organisers’ perspective, Wendy and I were both heartened to see the way every member immersed themselves in the initiatives despite the discomfort of having to be so forthcoming about showing appreciation.
I personally loved hearing about the random behaviours that arose which to me exuded fun and appreciation for the presence of another e.g. doing graffiti on window condensation during Coffee Roulette. The content of appreciation that was shared on Slack was also “of such high quality and full of heart, and people were engaged by leaving comments, etc.,” says Wendy. Members themselves had also expressed sentiments of feeling touched by the attentiveness and effort of their “angels.”
Clearly no matter how noble the intent and stress-free it may appear for those for whom it’s planned, these appreciation initiatives are not without its complexity and room for improvement. But as we count our small wins, they are the “goodness” that keeps us going.
Working with my weakness
Having had the privilege of helming Team Appreciation Month with Wendy’s direction over the past two years, I don’t presume the know-how (because the culture and needs of each organisation is unique, and there’s no shortage of ideas on the web or GPT). Let me instead share my personal experience, and how I get by with some of my own struggles.
If you’re thinking of organising a Team Appreciation initiative with a small team or doing it alone, may my confession be a lowly companion to the challenges one may find hard to broach.
Appreciation takes ̶p̶o̶s̶i̶t̶i̶v̶i̶t̶y̶ vulnerability
Embodying appreciation as a culture is a kick in the pants experience for me. That’s because the practice of showing appreciation is deeply uncomfortable for me, and quite unlike my usual character. As someone whose nickname at work was once Wednesday (as in Addams), it takes a well of vulnerability for me to find my definition of good in another and make a favourable stand for it. It’s going to appear too kind, docile and weak. Also, how is it gonna land? Am I gonna come across as awkward? Insincere? Dorky? Plus oof, accepting the appreciation from others rather than dusting them off on the count of “you don’t know, I’m not that good” is a whole other challenge.
Brené Brown describes vulnerability as “uncertainty, risk and emotional exposure.” It’s that icky, feeble, unsure feeling we get when we’re out of our comfort zone, often in something we have little or no control over. In my case, it is letting go of the control of the narrative I have of myself, as well as others. What about you? What makes you feel vulnerable, what do you have to let go of or embrace in yourself?
For vulnerability to serve us, it can’t just end there. Sadly and fortunately, personal growth has neither certification nor expiration; and it’s truly as cliché goes, a journey.
On my best days, I can only remind myself:
- Be kind to yourself, you’re growing in this area too.
- Be kind to others, you don’t know what they are going through.
I remind myself that my clumsy attempt may have a more positive impact on their esteem and mood scale than I selfishly think. (Matter of fact, I’ve been pleasantly surprised by the uncanny satisfaction my own kindness has brought me despite the initial hurdle.)
On most days, I still struggle. But it’s an awareness, not an excuse.
Trust the process (of planning)
Not only do I wrestle with myself when it comes to appreciation, I’m also a self-proclaimed wrestler as a planner, wrestling with my own plans.
The thing about culture being the lifeblood of an organisation — it is hard to perceive, harder to measure, hardest to change. Because of the multitude of considerations cum conditions to facilitate its “success,” planning feels simultaneously infinitely needful yet completely futile. Who am I for such a lofty task, what do I know?
Such a war against my malnourished sense of competence is no easy feat, but I take comfort in the words of Dwight D. Eisenhower, that “…plans are useless, but planning is everything.” Instead of trying to dig up my own grave of over-idealistic plans, I keep my focus on trusting the process (of planning).
When I find myself caught in an over-planning snare, I’ve found these notes-to-self helpful in trying to curb my tendency to over-plan because it’s my responsibility to do so, and doing anything less seems like “not doing my job”.
- Plan B is enough. Not sure if you’ve been there, but once there’s a Plan C, there’s always a Plan D, and soon you’re paralysed by the whole colony of plans. Make a good Plan B from the most likely alternative scenario, and make provisions for it. The rest we’ll handle as it comes.
- Keep your considerations factual. List the considerations that are important to you/the company, and write them down. They should be supported by evidence, and not a festering worry or unsolicited opinion. I also keep my list of considerations* thoughtful and lean.
- Know your priorities. Prioritisation helps make decisions about the way your program comes together when the temptation arises to cater to every need. There’s no all-encompassing plan, but there are plans that communicate clear priorities.
- It’s OK to empower. Not everything needs to be cast in stone and within grasp. Create sandboxes and allow for ground up choices to be made within clear boundaries (set time, budget, etc.). Refrain from auditing their choices, because agency is not agency if it is audited.
- Don’t be afraid to cancel your plans. Well-being and safety of your staff are not negotiable, but plans can be postponed or adapted. Even if it’s shelved, thank you for planning.
*Some things to think about when planning team appreciation or any such initiatives (not exhaustive)
- How’s the company doing? Is it stable and financially healthy, or is there restructuring round the corner?
- How’s the team dynamics and morale these days? Are there unresolved conflicts and brewing dissent you need to address, or perhaps they are still coming to terms with a colleague who resigned?
- What’s the cadence of work? Are there many upcoming deliverables you should consider, or has the team just concluded a project with a difficult client worth celebrating?
- What’s going on around you/the world? Are there political/cultural sensitivities you need to pay attention to, or are there environmental risks that should make health a priority?
- How are the individuals? Are they outdoorsy or do you need to be mindful of their social energy? Perhaps some time off is all they need (and we’ve done that).
Of course it’s all easier said than done. Even so, I am grateful for a kind and open-minded team who rolls along with the plans.
