December 29

How investing teaches social service strategy



I want to be clear.

I’m no Wolf of Wall Street.

Yes, I invest in stock markets.

But I’m not rolling in money.

Now you may think, so what’s the point of this article? If it’s not to help me get rich(er), then what’s the point?

I hope that the lessons (and mistakes) from 4 years of investing, can give you a different lens to look at your individual and organisational strategy within social services.

Who are you to tell me this?

And you might think, John… who are you to tell me this?

You rightly point out that I look quite young.

And yes, I’ve only had a year of experience working as a social worker in direct practice.

I’ve only had two years as a board director of a U.K. charity with an annual turnover of £11.2 million ($SG20.2 million).

Because let’s face it…

We are very uncomfortable with talking about money in social services.

Somehow, the idea of doing good, and doing good with money doesn’t seem to gel.

You see it playing out in different ways. Funders questioning why money needs to be spent on administrative roles or corporate capabilities. Or why money needs to be spent on raising money. Or whether staff are being overpaid.

It’s a charity, after all, isn’t it?

I might be wrong, but an unwritten rule is:

You’re doing charity, so don’t expect too much.

So this is the reality you face as a leader of a social service agency, or even as a staff.

Discomfort when talking about money or a pay raise or a new programme (that will cost money). Your boss shifts uncomfortably.

You sense resistance.

It becomes hard to craft coherent strategies when you struggle with questions like:

Where will money come from next year?

Will I win the bid for this service contract?

How do I continue running the agency, and yet reinvent it?

How do I transform, before I have to?

Does investing have some lessons for us in terms of crafting organisational and personal strategies, wherever we work?

I believe so.

I want to share my stock portfolio so you see that I have significant ‘skin in the game’.

This is not to say that you should buy these stocks.

Rather, I wanted to point out my mistakes.

And I hope it gives you a better framework to look at strategy within the sector.

Strategy is playing people chess, not people checkers.

In his framework of how companies move from Good to Great, business philosopher Jim Collins shares,

First who, then what.

Jim Collins, Good to Great

good to great framework

Great strategy is about playing people chess.

Playing people chess, rather than checkers, is acknowledging that each person you work with is different.

Each move you make (or don’t make) has significance.

It’s recognising the power of each chess piece. This is where chess differs from checkers.

In checkers, every piece is the same. Each piece has the same ability (or lack of).

But chess is different. Whether it be finance, human resource, or even the social service professionals, you don’t move them without fully acknowledging the strengths and weaknesses they bring to the table.

Thus, playing strategy like a chess game, rather than a checkers game, is realising each person’s unique ability.

Average managers play checkers, while great managers play chess.

The difference? In checkers, all the pieces are uniform and move in the same way; they are interchangeable.

You need to plan and coordinate their movements, certainly, but they all move at the same pace, on parallel paths.

In chess, each type of piece moves in a different way, and you can’t play if you don’t know how each piece moves.

More important, you won’t win if you don’t think carefully about how you move the pieces.

Marcus Buckingham, What Great Managers Do, Harvard Business Review

It’s about covering their gaps, and turning their supposed weaknesses into strengths.

Let’s say you’re struggling with a staff. People are raising all kinds of concerns with him.

It’s tempting to give him a performance improvement plan, and say to him,

Be like everyone else!

Follow the rules… or not…

Shape up or ship out!

What are the chances that he will continue being engaged?

But could you try something different?

Ask yourself:

  1. What if he was trying his very best?

It’s tempting to think that a low performer is messing up… because he’s lazy.

He’s just not trying hard enough.

But what if he was? What if he was trying his best, but that the fit isn’t there?

It’s tempting to blame it all on the employee.

But sometimes, it is two-way.

You are responsible to the employee by accounting for the agency’s actions that may be setting the staff up to fail.

The staff is responsible for taking the actions required.

  1. Where are the exceptions where he has succeeded? What about those conditions made that possible?
    1. Was it the people he worked with?
    2. Was it the type of project?
    3. Was it a particular set of skills he had been asked to use?

Play people chess. Respect individuality. Tap on the unique gifts.

Build conditions for people to flourish.

Successful strategy is in the day-to-day course correction.

Success is in the day to day actions, rather than a bold vision that galvanises everyone to work hard.

A bold vision is important. Daily, it’s important to remind yourself of why you are doing this work.

But it’s in the day to day that the course of the vision is worked out.

Think of it as a GPS. You start somewhere. You set the coordinates for your destination.

Along the way, you’re going to make a wrong turn.

The beauty of the GPS is that it calibrates, and re-calibrates. And it reminds you of how to get back on track again.

What are the practical steps?

Are there practical steps?

What’s worked for me is to connect the work of the teams I collaborate with to the larger vision of why we do this.

This doesn’t mean thinking high-level all the time.

But it means that at group meetings, I try to (with examples below):

  • connect smaller actions to the bigger work that is happening

This year, we’ve lost a lot. The ability to dance with our elderly. To drink kopi with them. To meet with them.

But I also see how we’ve continued to connect through online dance sessions.

And this builds on our work on connecting clients to communities. On combating loneliness within our elderly communities. On helping our elderly to love life, and love lives.

  • celebrate the progress of the team, however small it might be

Thanks James, I really appreciate that you were so efficient with getting this proposal out (pointing out positive actions).

Successful strategy is a habit.

The compound effect of small actions, lead to large effects.

You know this already.

But the question is:

Do you do it already?

We all know that certain actions, done consistently, will lead to outsized returns.

But I’m just a member of staff!

It’s not on my pay scale to think about strategy! Or to think about organisational change!

I’m just a member of staff!

You might wonder how strategy creation and execution matter to you if you’re a staff member. You might not lead it. And you might not have a say in how the strategy is crafted.

At some point, you will realise common frustrations.

It’s summarised below through Herzberg’s theory of what motivates, and de-motivates people.

My challenge to you is not to start an uprising.

But it’s to engage and converse with people in power about the issues you see.

It’s up to leaders to make the changes required.

But it starts with you seeing the problem, helping others to see the problem, and solving the problem we see.

Be active, not passive.

Okay, I confess.

I do complain about my boss with my friends.

No need to shift uncomfortably in your chair if you do. I’m not asking you to raise your hands if you do.

But what if…

As far as I am concerned, the problem is me. I am the place to start. Others’ responses will depend mostly on what they see in me.

The Arbinger Institute, The Outward Mindset

Try asking yourself that today.

Whatever problem you see… what if you had a part to play in that?

What if you had far more agency than you thought you had?

After 2 years of complaining about my bosses in the U.K., one day, it dawned on me.

Complaining was entirely useless.

Nothing changed.

It was like stepping on the accelerator whilst the car’s gearbox was in neutral.

I created lots of strain in myself. But nothing moved.

Any meaningful change comes with effort.

Not complaining about effort.

Manage your boss.

I hope we’ve managed to get some resistance out of the way.

At this point, if you’re looking for some mind-bending tricks to make your boss do what you want, I don’t have them.

I only have evidence that works.

  1. Do you know your bosses’ working styles?
  2. More importantly, do you try to fit their working style?

During my student placement in Nottingham, I used to have a supervisor who loved typing me long emails, with her comments about an assessment I did.

I preferred to have a chat.

Wasn’t it better to have a quick and snappy chat, rather than typing emails to each other?

But I failed to make the distinction between ‘readers’ and ‘listeners’.

In his classic article, “Managing Oneself“, management guru Peter Drucker classifies people into ‘readers’ and ‘listeners’.

(Readers prefer) … information in report form so they can read and study it.

(Listeners) … work better with information and reports presented in person so they can ask questions.

Gabarro and Kotter, Managing Your Boss, Harvard Business Review

To create a thriving working relationship, you need to know your boss.

And you need to work with your bosses’ working style.

You create the change you want to see.

And you change according to the change you desire.

Learning to quit

I bought a stock named Sino Grandness in 2018. They sell juices in China.

I bought it at $0.20 per share.

A year later, it was $0.02 cents per share.

Screenshot from

At that point, I asked myself.

Was I willing to admit that I made a mistake?

After great pain and deliberation, I sold it at a 89.7% loss.

5 months later, the company faced investigations over its accounting and was suspended from trading.

The point of this story is not to show how bad an investor I am (though I still am).

It was a lesson on learning to quit.

As human beings, it’s not easy for us to admit our mistakes. It’s painful.

But in our individual, day-to-day work, it’s easy to get attached to the programme we run, the difficult clients we see, the colleagues we work with.

It’s not easy to say:

It’s not working out.

Learning to quit is not about learning to give up. But it’s about recognising that you are human. And that you will make mistakes.

Sometimes, the programme you run is not going to work out. More time, more effort, more money might give it a temporary boost.

But in the long run, is it going to work out?

When I face decisions about quitting, two things help me to clarify my thoughts.

  1. A pros and cons list

As humans, our brains are not built for decisions like today’s. For thousands of years, the most difficult decisions we had to make was:

Is this safe to eat?

Am I safe here?

Listing out the pros and cons brings rationality to what can be an emotionally difficult decision. I’m not saying that you should ignore your emotions and your gut.

But I’m saying that you should be aware of how your emotions can lead you to a bad decision.

  1. Asking myself, ‘Would I be willing to sit with this for another 5 years?’

Projecting into the future prevents you from falling into the autopilot trap. Organisations can fall into the trap of putting off painful decisions, kicking them into the long grass, because it doesn’t hurt enough (yet).

But if you project yourself doing this for another 5 years, it makes things clearer.

It can be in your personal life too.

Many of us know that we should exercise.

I look down at the pudge in my belly. I look at the rain outside. Then I think, oh that’s too much effort.

So I sit with it for another day.

But for another 5 years?

What would happen?


Strategy sounds like a big word. It’s too high level!

But I hope this has convinced you that strategy is not that high-level thing that your director professes, but that few are a part of.

Rather, it’s something that clarifies the end we want to reach.

And how we will reach there.

The question is…

Are you ready?


What helps you to clarify and execute your strategy in the agency you’re part of?

What helps you in executing your personal strategy?


This article and the financial advice within, in no way, constitutes advice accredited by any monetary authorities. Please do your own due diligence before acting on any advice within.


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