Asia's Premier Speaking Coach for Corporate Senior Leaders and CXOs

I help business leaders create and deliver modern communication and messaging strategies with presence, power, and purpose.

How to Connect with People in Authority

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Ever since I have written the article on ‘What I wish I knew (earlier) when I stepped into University’, many have asked me how they can likewise connect with people in authority like their professors, deans, bosses, entrepreneurs, senior management and C-level executives. Most of the people who asked, had issues in terms of how to initiate contact, fear of how the relationship may go awry and that the very people they want to connect with may just turn them down.

I write this entry to shed some light on these issues so you know what’s in your way in connecting with people in authority. For those who are in love with structures and methodologies, I have framed this subject matter into the 5W1H in order of relevance and how you should go about approaching this process.


Simon Sinek, a thought leader best known for his “golden circle”, has decoded a seemingly esoteric concept called ‘intention’ by advocating that we start with why. It’s almost intuitive that before you begin with any task, project or job… ask yourself why are you doing this?

The rationale behind connecting with people in authority is simple – you like to seed a relationship that can support you in your growth and also, be in a position to give back to this person who will be investing their time and energy in you. It could be in the form of a mentoring relationship, to request for feedback and improvements for your performance or just seek a sounding board for your ideas.

Remember, you take ownership of your own learning and growth and connecting with people in authority is one way you can do so. In my experience, it is also one of the most expedient ways to get introduced to larger networks and pools of shared knowledge so there are many merits in this undertaking.

The last thing you want to do though, is to have an ego trip because you managed to pull off a luncheon with your big boss and go around bragging about it. When the word goes around, be warned that you may just get more than what you have bargained for.


There is beauty in both commonality and diversity. As my personal rule of thumb, I tend to want to connect to people who are either better, if not superb, at what I am currently doing or that they are engaged in an art or skill or field that I seldom have contact with but have that wee bit of interest to explore in.

The former allows me to deepen my awareness in the specific areas of mastery like entrepreneurship, public speaking, coaching and activism. From such interactions, I get to learn more about potential pitfalls and mistakes that I can otherwise avoid making. The latter allows me to expand my horizon, shift my paradigms and see the world in a whole new different lens.

A recent link-up with an architect made me discover that the perception of physical spaces can be transformed radically just with a simple change of a tile. After that encounter, it was as if a new dimension of appreciation and awareness has opened up for me in my world as far as appreciating the little things in life that I otherwise often overlook.


Time is a precious commodity to people in authority hence you want to be specific about what you want to get out from the meeting and how much time your meeting, meal or coffee session will take. For example,

“Hi Derek, it was great pleasure and honor to have met you at the Entrepreneur’s mixer yesterday.

In fact, if your schedule permits I’d love to buy you coffee and seek your insights on a business idea I am currently working on. I believe our session will not take more than half hour and so if you will, please let me know two timings that will work for you in the next two weeks and I’ll do my best to fit in.

Thank you.”

For starters, you may want to prepare a list of intelligent questions that you could ask to keep the session to the point and succinct. However, also leave some room for flexibility for you never know in what direction the conversation can move in.

During the meet-up, it can be slightly tricky as to what you should and can do to start and manage the conversations. Some people would like to engage in the usual small talk to find out more about you first while others have to talk shop before transiting to trivial everyday matters. I generally let the other party lead the conversation and then flow along with the tone and style of conversation.

It is important to you to be present (in the here and now), curious, interested and open. If not, why would you initiate contact in the first place?

Some of us would be afraid of (awkward) pauses especially when the other party is reflecting, introspecting or taking some time out to reply a text message. Do not be tempted to fill in the spaces because you may just interrupt his or her train of thought or worse still, finish up the sentence for the other party. Be conscious of these tendencies and get a hold of yourself.


Technology has made connecting so much easier. In the past, a phone call will be the preferred mode of communications but you run the risk of having rejections or catching the other party at the wrong time. I usually only give the other party a ring when I feel I need to be more sincere and personal and hence I have to relate with the person over the phone or to follow up when the emails have not been picked up on. There is however, no hard and fast rule to this.

Linkedin for example, is another great platform for young people to get acquainted with people in authority in a wide spectrum of fields and specializations. Sign up for an account if you haven’t! It also helps that you have a complete profile with a couple of recommendations as some people tend to be more discretional and would want to “screen through your profile” to have a quick sense of who you are before meeting up.

This is a request I had sent previously from my Linkedin account to connect with a corporate executive who has taken an interesting career trajectory.


Chances are that if you want to connect with a person in authority, you want to try your best to fit into his or her schedule. But my suggestion is do that within your means and be wise about it too.

Also equally important is when the other party requests that you follow up some time down the road like a month later because he or she has no or little awareness of the schedule ahead, do so. It is grossly irresponsible and rude for you to initiate contact and then have the person in authority chasing you for the meet-up because you have forgotten to follow up.

I have been on the other side of the table and usually if the other person does not bother checking in after the time period I have suggested, I take it as a non-interest and move on to more needy matters in my life.


As much as it sounds like a no-brainer, there are a couple of areas you want to consider when it comes to the location of the meet-up.

It is highly unlikely you will go wrong with the usual haunts like Starbucks, The Coffee Bean or The Coffee Connoisseur (TCC). But I generally leave it to the other party to decide because one, it is for their convenience and two, if the other party is picking up the bill (they normally do so as a show of their seniority and goodwill), I do not want him or her to get a rude shock when the bill comes or frown upon a place that’s not so befitting for the other party (like how the hawker centre may not always be the best place to meet a CEO).

At the end of the day, have faith for the person you are enjoying that steak or a cuppa latte with is still a fellow human being, albeit with more successes, experiences and wisdom. Treasure the time and energy that he or she is willing to invest in you and make it count.

Likewise if for some reason of the other, the contact doesn’t work out – run through the 5W1H again and start with why. Chances are if your intention is pure and sincere, it is only a matter of time so just be patient, my friend.

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