5 Things I Learned About Leadership as President of the Cayman Islands Chamber of Commerce

We learn leadership in school and college, through life lessons and mentors, and through reading and example. In this post I want to share with you five leadership lessons I learned (or had reinforced) while President of the Cayman Islands Chamber of Commerce.

This past week I completed a year as President of the Chamber here in Grand Cayman. I was given the trust and opportunity provide my leadership to the organisation in its 47th year and worked to ensure that everything I did honoured and built on the leadership legacy framed by the many presidents before me. Basically (and sometimes basic, direct language is the best) I did not want to muck it up!

The record of accomplishment for the year is available on the Cayman Chamber website (the Annual Report will be posted shortly). This post, however, is less about the Chamber and the past year’s activity. It is, rather, five key leadership learnings I gained, or had reinforced, over the past year, and in particular leadership of a voluntary or not-for-profit organisation. The Chamber council (board) and executive leadership is 100% volunteer and non-paid, and the day-to-day activity is run by a paid CEO and staff of four. I believe these learnings translate well into other volunteer and not-for profit groups, and indeed, commercial business leadership.

1. You can please some of the people some of the time but not all of the people all of the time. I don’t ever recall deliberately becoming one, but on reflection I think I am a consensus builder. When a decision is made I want to make sure that all are behind that decision and, even if they were not for it initially, can now support the decision made by the group. Newsflash…that rarely happens. It incredibly hard to get all stakeholders aligned on an issue or decision. The Chamber probably does it better than most, but even there it can be challenging as the organisations work touches on politics and larger business and societal issues. The issue is just as real, however, on a small school PTA, a social group or a service club. It can be really challenging to discern the true motivation behind some objections. Often objectors to a course of action do not speak directly to the leader of an organisation on an issue, going through others to express concerns.

The lesson? Do it anyway. As long as your decision has the support of a majority of your board or leadership, and directionally moves the proverbial ball closer to attaining of the organisation’s strategic objectives, then do it and don’t look back. You can’t fault right in the long run.

2. You can’t repeat your vision often enough. I have not made much of a secret of the value I place in continuing learning in areas that you is interested in (see item 5 in this post I wrote). This blog is the direct result of learning I have received from Michael Hyatt’s blogs and podcasts. In this transcript of a podcast he gives clear direction on creating, and sticking to a vision. I recall one day repeating in a talk I was giving my mantra of the past year, “respectful advocacy”. For a moment I thought to myself, perhaps I am overdoing that line a bit too much. In an instant I recalled a podcast by Michael where he noted that when you start thinking that you have said enough on the vision you are trying to instill within your organisation or company then you are probably about half way there. That really resonated with me. You just cannot express your vision enough. We live in a world with perfectly lovely people who can articulate the problems around them, describe the faults of others and complain of the challenges with getting their wi-fi to work on their flight to Miami. For some reason, however, they cannot articulate a vision for where they wish to take the organisation they lead.

The learning here? Know your personal objectives and align them with the strategic objectives of your organisation. And everyday, everywhere, tell the story. In demonstrating leadership of your organisation you can’t articulate the vision enough.

3. Shut up and listen. My business has had the benefit of coaching delivered through Shirlaws Cayman since March of 2011. One phrase often used by our coaches rings in my ears when I have the urge to speak over someone or am moving too fast on an issue for those on the fence to feel connected and supportive. “Slow down to speed up.” This is not an easy thing for an entrepreneurial person to do. Urgency is our byline. Now is too slow for most leaders. One of the best lessons I ever had around this concept of listening came from a sales professional who mentored me. Simply put it was to a) ask questions of the client, 2) listen to the responses, 3) make a sales proposal based on those responses, and KEY POINT 4) shut up and listen. Don’t ever be the first to speak after asking for the sale or you will lose the sale. This sales example is just as applicable to a boardroom setting where you are working to advance an agenda item. Take the time to listen to all of the issues raised by all stakeholders. Seek input that gets to the root of why an objection may exist. Ask what solutions the objector may propose. Then, shut up and listen for the flow of information.

Takeaway point? We all want our cause to succeed. Listen for the objections that can impact the success of your cause or agenda item. Take the context a bit higher to see where both parties can agree and gain success. It works.

4. Focus on the goals. Having a goal, a strategic plan, or some form of a roadmap to where your organisation intends to go is critical to the success of an organisation. One of my favourite phrases comes from chapter six of Lewis Carroll’s ‘Alice in Wonderland’. Alice, alone and confused at an fork in a road was asked by the Cheshire Cat if he could assist her. “Where are you going”, asked the Cheshire Cat?” “I have no idea,” replied Alice. “Well,” said the Cheshire Cat, “take any road you want. If you don’t know where you are going, any road will get you there!” This simple statement is quite profound if you take a moment to dwell on it. Without a goal, an idea of where you wish to end up, the attainment of the organisation’s objective is impossible. How can you achieve a goal that you have not articulated? The Chamber works off a revolving, multi-year strategic plan and consistently hits its objectives. The success then is no accident as it is planned for. Things will come up that change the course in the short-term. Annually the leadership will change and a different focus area may be applied. However, a longer term set of strategic objectives that bridges multiple years keeps the organisation keenly focussed on the future.

Application from this point? Write down your objectives. If your organisation does not already have one, get to work on a strategic plan or a set of organisational objectives. In your personal life, write you personal goals for different life stages. Without this you are subject to drift, lack of real accomplishment, and the unfortunate emotion later dreaming of ‘what could have been’.

5. Appreciate the ones who do the work. The leader of any organisation is there to articulate the vision, to hold the context of the organisation (the ‘why’ of its existence), and to steward its resources for the attainment of the goals and objectives. In a voluntary organisation the reality is that the leader is typically not the doer. I believe it is essential to acknowledge and publicly thank those who take on the task of administration for an organisation in a paid capacity, and those who head up various committees and task groups. In a way this post may be my most public and lasting statement of this appreciation. A year out of university I started working for Esso Standard Oil. Possibly the most important lesson I ever gained in leadership was not gained in a formal classroom setting. It was the learning to give genuine appreciation and that leadership lesson was taught to me on the forecourt of a gas station during the Cayman visit of the Florida based sales manager. These annual events normally involved a tidy up of the station, all the staff having sparkling new uniforms, and the dealer being ready to receive the entourage. We would all arrive at a station and go directly into meetings with the dealer. With a few of these visits under my belt I expected that the visit by the new manager just posted to Florida from France would be no different. How wrong I was. Almost as soon as he got out of the car we lost track of where he was. Then, looking over at the pump attendants I glimpse him darting from one attendant to the other shaking their hands and introducing himself in the thickest of French accents to the local pump attendants. Oh, and thanking them for all they do for Esso and for the dealer. Wow. Later, when I asked him about why he did this he said that it was those guys that made the station successful. They know the likes and dislikes of the clients. They know if a customer has not been in for a few weeks and may be buying elsewhere. They are the lifeblood of the gas station yet these guys are so often overlooked and taken for granted. This was real leadership. These gentlemen would have done anything for that sales manager.

The life lesson here? Thank them. Thank everyone who helps you as you make your way through life. Thank all who assist your organisation in the realisation of its goals. Give them all the credit for it can not happen without them.

What are some of your leadership lessons that you have gained from your past work or volunteer experience? Share them with me in a comment.

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I live in the Cayman Islands and I'm married to Christina. We have two incredible children, Ryan, attending Northeastern University in Boston, MA, and Taylor, attending Trinity College School, in Port Hope, Ontario, Canada. I own several businesses in Cayman. My list of 'pasts' include past chairman of the Cayman Islands Special Economic Zone Authority, past president of the Rotary Club of Grand Cayman, and past president of the Cayman Islands Chamber of Commerce.

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One thought on “5 Things I Learned About Leadership as President of the Cayman Islands Chamber of Commerce

  1. Sharing, learning, humility (as displayed by you here) are all traits of a leader others will follow. Oh, and also leading by example. Would love to see other leaders engage and share in this way. Keep on sharing, David !