We all prepare carefully for our ‘ask’ conversations, but meaningful conversations happen every day. Learn how to make all your conversations deepen your relationships.


“As practitioners in philanthropy, our world is made up of conversations, some of which are harder to have than others, all of which are critical in one way or another.”

A few weeks ago my three children returned to school after the term break. At the end of the first day, I asked my youngest son the question that was no doubt being asked in homes all over Singapore that day. The conversation didn’t go as I expected.

Me: “How was your first day back?”
Son: “Intolerably boring”
Me: “Why was it boring?”
Son: “I went round all day with a face like this.” (Pulls a face with narrowed eyes and a down-turned mouth like Robert de Niro in Goodfellas.)
Me: “Why did you have a face like that?”
Son: “Well, I’m beginning to become skeptical about school. I mean, what’s the point?”
Me: “Do you not think getting an education is an important part of life?”
Son: “I didn’t say I was skeptical about education, I said I was skeptical about school.”
Me: “Well, fair enough, but education is important and you still have to go to school tomorrow.”
Son: “I hate school.”
Me: “You can hate it if you want, but you’re still going tomorrow. Time for bed.”

Reflecting on this, the latest in a long line of conversations that end in some variation of “Because I’m your mother, that’s why”, I thought about how little we prepare for conversations that might uncover really important issues and that are in fact critical for both parties. My son is only eight years old – he shouldn’t be skeptical about school (at least not yet). I should have been more ready for that conversation, and when it came I should have recognised the opportunity and helped to uncover the deeper issues for him.

As practitioners in philanthropy, our world is made up of conversations, some of which are harder to have than others, all of which are critical in one way or another. Conversations allow us to create safe working environments for our teams; they create connection and belonging; they connect us to our higher purpose; and sometimes they lead to donations that transform our institutions for the better. In short, we all need to be really good at the art of meaningful conversation. And yet we jump into conversations, sometimes with no planning or thought ahead. Before we know it, somebody is refusing school.

So here are my top tips on how to prepare for a meaningful conversation:

  1. Remember that our fundamental goal in conversation is to strengthen relationships. Solving a problem or unpacking an issue may be an outcome but they should not be the only focus. This is especially important in difficult conversations where you need to speak truths that might be hard for others to hear. When done well, these conversations strengthen the trust between two people. Knowing that you trust and respect me enough to tell me when and how I am going wrong builds trust between us. And if you frame it not as ‘Here’s your problem, what are you going to do about it?’ but rather as ‘Here’s the problem, how are we going to solve it together?’, then we can face the challenge together.
  2. Be vulnerable. There is a proven link between vulnerability and cooperation. Dr Jeff Polzer, a professor of organisational behaviour at Harvard, identifies the ability to say that you need help as the first step in building trusting relationships. We don’t show our vulnerability after we trust people: we show our vulnerability first, they (hopefully) respond with their own vulnerability and trust emerges from the mutual need for each other’s support.
  3. Don’t assume the problem or issue is known. Enter into the conversation wanting to explore the topic together and accepting that there might be things you are unaware of and deeper things at play. The relationship won’t strengthen if you have a fixed goal that you never deviate from. Listen carefully.
  4. Get really good at paraphrasing. There is not enough space here to go into the power of paraphrasing, but of the three types of paraphrasing (acknowledging, organising, abstracting), I have recently seen the tremendous power of abstracting. A colleague, who was struggling to explain why his Line Manager supportively sitting next to him as he completed tasks was a problem, had a breakthrough when I was able to say “So for you this is a trust issue”. Articulating a problem that someone was not even aware of themselves is at the heart of many transformational conversations.
  5. Consider the motivational interviewing technique. Let’s say I want to persuade a reluctant leader to commit to giving their time or resources to a fundraising project. I ask “On a scale of 1 to 10, how likely are you to commit to this project?”. The reply might be “Well, I am really busy at the moment, so right now maybe a 4.” My natural instinct might be to respond “Well, how can I move you to a 6 or a 7?” But, according to Michael Pantalon at Yale University, an expert in the art of persuading and influencing, the best next answer is the (seemingly irrational) “Why didn’t you choose a lower number?” This allows the other person to explore their own motivation to commit to the project, rather than their justification for not doing so.

The art of conversation is complex and these tips are only the tip of the iceberg (ahem). It turns out my son has been finding it hard to identify a partner in his class who wants to work the way he does. And the reasons for that are the next conversation I’ll be having with him.


Sinéad Collins, Director of Communications and Marketing, UWCSEA

Sinéad began her career as a performing musician and teacher in Ireland before moving to China and then to UWCSEA in Singapore, one of the leading international schools in the world, where she leads strategic marketing and communications. Most recently, Sinéad spearheaded a pilot impact study for UWCSEA, in partnership with Harvard GSE, which is now a significant longitudinal study.


Sinéad will be speaking at the CASE Asia-Pacific Advancement Conference 2019 in April.


Thinking Collaborative (2019) Three Types of Paraphrase

Coyle, D (2018) The Culture Code Random House, New York

Pantalon, M (2011) Instant Influence, Little, Brown and Company, New York



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