Diligent Delegation | The Decision to Entrust

Entrepreneurship is the adventure of a lifetime.

The first two years of any new venture is a chaotic blur of doing what needs to be done. Like a jack of all trades, you end up doing a little bit of everything. Through this journey of juggling and multitasking, you discover skills and talents you may not have known you had.

As an enterprise grows and stabilises, the game changes. As my businesses started expanding, I needed a team who could serve our customers. The foundation stone of any business is to serve its customers.

I remember the incessant stream of customers from all over the world who would flock to my family’s store in Singapore’s historic Kampong Glam district. Back in the day, my great-granddad entrusted me with the task of collecting money and giving our customers the appropriate change. As I grew older, I was entrusted with bookkeeping and with time I was entrusted with the task of managing the finances of the business.

To entrust is to assign the responsibility of doing something to someone. In modern-day lingo, this is called ‘delegation’.

Delegation is a decision-making process that allows the leader and every member of the team to focus on doing what they do best. John C. Maxwell, the author of Developing the Leaders Around You writes, “If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.”

The very act of entrusting someone with a responsibility requires that they are able to take 110 percent of the responsibility for their piece of the puzzle. They need to be able to go above and beyond what is required for that particular role.

As someone who was once in charge of the finances, I was not expected to do stock takes, sales or even maintain customer relationships. That was not my piece of the puzzle. But I knew that I had to do my very best with the puzzle piece that was assigned to me.

The Master Craftsman

An individual contributor is someone who has gained a certain level of mastery in their craft. They are experts in their field and often have apprentices working under them.

Two prerequisites are necessary for anyone to gain a certain level of mastery in their craft. They are the twin pillars of knowledge and experience.

Knowledge is the first pillar of a master craftsman. Lawyers need a law degree and accountants need an accounting degree. Plain and simple. There are certain professions where without the necessary education, you simply can’t practise.

Do not confuse high-potential candidates with the master craftsmen. High-potential candidates are individuals who need to work under master craftsmen till they are ready to work independently. To distinguish those with high-potential from those who have manifested it in real world terms, ask yourself:

  1. Does this potential team member have the knowledge that is necessary for them to do their job?
  2. Is their experience relevant to the job they’re applying for?

Let me illustrate this point with a simple example. All businesses need accountants. There is, however, a significant difference between a financial accountant and a forensic accountant. Whilst a forensic accountant would obviously have knowledge about financial accounting (and vice versa), their day-to-day responsibilities and specialisations vary considerably. You simply don’t go to see an eye doctor when there is a problem with your foot.

Once you’ve established that a prospective candidate has both the paper qualifications and experience that is necessary, it is time to ascertain whether they are a good fit for the long-run.

Ask them about their goals for the future. Are they aligned with the needs of the business?

It’s not uncommon for people not to know what they want to do five years down the line. But what is their plan for the next year or two? Are there open roles within the organisation that they’re interested in? Allow them the opportunity to do a ‘work experience’ or even ask them to come up with a prototype of a project they might want to pilot.

How do they deal with the feedback that they receive on their projects? Are they able to make a comeback? Or do they run away at the first sign of difficulty and rejection?

That’ll give you a good idea of what you can expect if you had them as part of the team.


Without trust, nothing grows.

Trust is a two-way street. A two-way act of faith. An angel investor I work with quite closely has what I call a very strong ‘trust radar’. To him, trust develops and grows over three stages.

Stage 1

The first level of trust is between individuals. Is this person’s heart in the right place? Why has this person chosen to work for the organisation? Is it to advance their own personal goals or to contribute to the organisation? Are they a team-player or… not?

It’s really that simple.

Leaders are part of the team, but they’re not team-players. Leaders come in all shapes and sizes. Some leaders are authoritative, others democratic. The onus is on the team member to ‘manage upwards’.

Is the team member contributing to the organisation’s goals or are they making the leader’s job more difficult? Managing up goes beyond just ‘getting along’ with your boss. It’s about forging such a strong relationship that your boss will go above and beyond to ensure that you succeed in the organisation.

If you feel you’ve ‘failed’ or not had the success that you were looking for, it’s easy to blame the leader. But the problem is usually not the leader, but the way you ‘manage up’.

Stage 2

The second level of trust concerns competency. Can I trust this person to do their job without my supervision and help? In most organisations, people get a couple of weeks of training and then they are on their way. If several months later, an individual is still looking to you for all the answers, then they are incompetent. Plain and simple.

Each team member must own their slice of the pie. If they don’t contribute to the pie, they have no claims on the rewards that emanate from it.

A team is only as good as its individual puzzle pieces. The individual pieces come together to achieve more as a team than they ever could alone. You will know when you find this person. You’ll be so pleased with this person that you’ll gladly give them a raise and a promotion to reward them for their hard work and the contribution they have made. You will be singing their praises to everyone and will never want to stop.

Stage 3

The third level of trust concerns evolution. People are constantly changing. Organisations are constantly evolving. Is this individual supportive of the inevitable changes that are occurring or are they trying to hold the team and the organisation back from achieving their long-term goals?

Change is a normal byproduct of working in an unpredictable environment. No business can afford to stay static doing the same thing day in and day out. It is true in nature and true in business. Seasons change. Markets change. Products change.

We either evolve or get left behind.


Ask any leader and they will tell you that this is a big one. Sometimes you can have the right person with the right skillset, but they simply don’t fit in with the organisation you’ve built or are building.

For instance, corporations have a distinctly different culture to family-run organisations. Institutions such as government bodies, schools and places of worship also have a different modus operandi.

In corporations, the Board of Directors represent shareholder interests. The BOD creates company policies and the management team is responsible for enforcing company policy and holding employees accountable for their actions. People who run the organisation need a variety of skills that are distinctly different from those of board directors. In family-run organisations, the people managing the organisation will typically be the owners.

The ownership structure strongly influences how decisions are made, who is making them and why they are being made.

In addition to the ownership structure, have a think about what the culture in the organisation is like. For instance, in Japan, where I worked for four years–the culture is still largely hierarchical. Seniority is based on age, experience and how long you’ve been in a company. I also very rarely had personal relationships with colleagues outside work.

When I lived in Australia, on the other hand, egalitarian-style camaraderie is the norm. You may well grab a drink with your boss after work, even though there is no obligation to do so. People speak to each other quite casually and there is no real sense of hierarchy–but it does exist–albeit in a highly informal way.

As for me, since I worked in a family-run organisation for decades, the boundaries between personal and professional didn’t exist at all. I knew the people I worked with extremely intimately. This is not the norm in most places of work where the personal and the professional have a way of existing in two separate boxes. To a lot of people, work is just work and has nothing to do with family.

Whether it’s a family-run organisation or a large corporation, I firmly believe that when it’s time to work, it’s time to work. I don’t believe in anyone using a personal relationship to advance personal agendas or enjoy kickbacks at work. It is still the best ideas that need to win–regardless of what the culture is like.

Diligent Delegation

Delegation comes down to trust. Can you trust the people in your team to do more together than they ever could alone? Or are they simply creating more work or problems for you?

Each team member is going to face their own personal and professional challenges no matter which organisation they work in. The real question is: are they able to overcome those challenges and thrive in their new environment?

Entrepreneurship is the adventure of a lifetime. I can’t say I chose this path. It chose me. Growing up, I harboured no grandiose ideas of being a leader. I was content with being the family accountant and I was good at it. The journey from being an individual contributor to an enterprise leader was not one that I ever expected that I would ever be on.

But here I am. I love my current team… but I can’t honestly say that this has always been the case. I’ve had team members who did nothing but create more work for me and add more items to my ever-growing ‘to-do’ list. Over time, I grew increasingly exhausted and burnt out.

Entrepreneurship is meant to be an adventure, not a slog or a daily grind. With the right people by your side, you can celebrate the victories, enjoy the journey… and overcome any obstacle or obstruction that dares to rear its ugly head.

The decision to delegate has its roots in entrusting people to do what they do best... and to do it in such a way that the sum of the individual pieces will always be far superior than its individual parts.

About the Author

Dipa Sanatani is the Publisher at Mith Books and the author of The Little Light and The Merchant of Stories. In The Merchant of Stories, Dipa takes the reader on a personal journey–narrated through a series of candid journal entries–on what it takes for entrepreneurs and creatives to start their very first venture.


13 thoughts on “Diligent Delegation | The Decision to Entrust

  1. A good boss is a blessing that you often don’t appreciate when you’re young and inexperienced… Which is why the bad experiences stay with us for so long. Your boss is your friend only if you first learn to be a friend to your boss.

    Liked by 5 people

  2. You know, when I was a boss, people said many unkind things about me and to me. What low-performing employees don’t realise is that they treat us like mum/dad/teacher whose job is to nurture and groom them. We’re here to manage resources, not monitor bad behaviour. The more difficult they make life for their boss, the less likely they are to succeed in any organisation. Excellent leaders are not swayed by sugary words–they’re looking for people who know what they’re doing and can do it well.

    Liked by 4 people

    1. Our earliest model of ‘leadership’ is dad/mum/teacher–unless you actually worked for them, as was the case with Dipa. Our parents and educators work for us, not the other way around. Leaders work for the organization as a whole, not its individual parts. — G. Michael

      Liked by 3 people

      1. Most parents want to give their kids everything they never had. Few parents have the discipline to give their kids what they need to succeed. That’s why ‘reality’ ends up feeling so harsh when it ‘kicks in’. But it was always there, they just weren’t exposed to it.

        Liked by 1 person

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