Influencing Powerful People – Lessons Learned from a General Counsel’s Career

Author: Michael P.J. McKendry | | Categories: Influence , Influencing Powerful People , IPP 2.0 , Power

Blog by Jenoir International Inc

Special thanks to Michael P.J. McKendry for this blog entry. It is part of the IPP 2.0 Blog Series, which revisits the “rules” introduced in Dirk’s book Influencing Powerful People and invites experts from various sectors to share their perspective on the topic. Michael is a recently retired executive with almost 30 years of diverse legal and business experience within multinational corporations and a large law firm.

I recently retired from a position as VP Corporate Services, General Counsel & Corporate Secretary at an industry leading international manufacturing company. Prior to that I worked at a leading global consumer products company and prior to that at a large law firm in downtown Toronto. For close to 30 years I came into contact with clients (both external and internal) who were often powerful in any number of ways, including those who were: important within the organization in which I was employed; important within society; superiors within the organization; powerful and/or domineering personalities; entrepreneurs who ran their own businesses; political figures; or even stubborn and headstrong individuals that could be intimidating to deal with as a client in either a law firm or a corporate setting.

Looking back there are some lessons that I learned along the way that I wish I had known earlier in my career, and my life, as I was grappling with how to effectively dispense advice to these “powerful” types of individuals in order to (a) provide them advice in a way that would help them make appropriate decisions; and (b) influence those decisions to achieve the best result for the client or the organization with which I was employed. It is important to point out that as a legal advisor for a company your client is the company, not those individuals working for that entity. Over the course of my career I often had to remind individuals within a corporate environment that they weren’t in fact my client even though they sometimes believed that to be the case. I was there to protect the organization and to give advice that was best for the organization and its divisions, not to individuals. However, it is often a fine line between providing the best advice for your “client” when advising some of the most powerful people, such as the leader of a business unit, a Chief Executive Officer, a Board of Directors, or even the founder of a company.

Never lose sight of your values

Many years ago I was asked by a powerful leader to do something that I believed was inappropriate. I was young and could have been easily influenced to do something that I would have certainly regretted, both at the time and later in my life and career. Powerful people don’t always have the time to assess all aspects of a situation or the potential impacts of what they are trying to achieve. They may not realize that something is either illegal or even just morally wrong. In this instance, the first time a suggestion was made to me I simply laughed off the request. I went away wondering whether the leader had in fact been serious. I concluded that there was a real risk that the leader did in fact wish to do what he had requested, and that there was a very strong chance that I would be asked again in the near future to implement his suggested approach. I prepared myself for the next interaction. I internally debated endlessly how to respond should I be approached again. On the one hand, I knew that I felt uncomfortable about the request and should simply advise the leader I could not do what he was asking. On the other hand, I knew the individual was powerful enough that he could determine my career progression and indeed my fate within the organization. Sure enough, several weeks later I was approached, and again asked in a slightly different way to do something that I felt was wrong. This time I was ready. I did not laugh off the request. I suggested an approach that I knew the powerful person was uncomfortable implementing. The approach worked because I made clear that I would not do what was asked of me, yet also suggested an approach that could ultimately accomplish, in a different way, what the leader wanted to do. Looking back, I believe there was also another important benefit that was attained. This early interaction sent a very strong message that I wasn’t willing to be used as a puppet, especially for incongruous purposes, and I believe it gained me some measure of respect. While I had not exactly said no to the leader, I had suggested an alternative workable solution that was also within the limits of my established values, which the leader ultimately appreciated.

Avoid saying “no”; instead say “What about trying this?”

We often hear stories about how important it is to stand your ground and fight for your position. However, that advice does you no good if your opinion is no longer desired because you become perceived as someone who cannot provide workable solutions to everyday obstacles that arise in business. Saying “no” is not always the best approach and should only be done in certain instances when necessary, such as a request that goes beyond your personal values or integrity or an illegal activity. I learned early in my career that powerful people are typically not the types of leaders or individuals that want to hear the word “no”. They have often heard that their plans or ideas do not have merit and that they will likely fail, but they have the confidence to proceed in the face of obstacles and naysayers. Rather than saying “no”, coming up with alternative approaches and advising that it would be better to proceed another way instead, is more impactful. Sometimes an alternative approach can even provide an additional benefit to be gained. Being perceived as a business partner willing to find workable solutions, will typically result in powerful people requesting your assistance more often in the future rather than planning your early exit from the organization.

Don’t just blindly do as you are told.

During an economic downturn, and as a leader of multiple functional areas, I was tasked by the CEO and the Board with eliminating a certain number of roles within the organization. On the one hand, the number was daunting and the exercise was potentially detrimental to the continuation of the areas within my group providing functional support to the business. On the other hand, the reduction in overhead costs was crucial to the organization’s cost structure and therefore the ongoing continued operation of the company. Rather than simply do what I was told and cut jobs, I took some time to conduct an analysis and formulated a plan to synergize roles within multiple groups so that previously individual functions could be combined to take on additional responsibilities. These new roles meant that only a few jobs had to be eliminated rather than the larger, significant target that had been proposed. It was a win-win scenario, and the lesson learned from the experience was rather than doing exactly as I had been told, think outside the box to find a solution that could work for the company and those involved. All too often we do what we are told to do, particularly when the request is coming from someone in a position of power. We sometimes fail to question, in a respectful and appropriate way, what is at the root of the request and whether we have to do exactly what we are being tasked to do. Blindly following without analyzing the situation is the enemy of innovation and creativity. Despite their requests, which can at times seem more like forceful demands, powerful leaders do not typically hire people to have their requests followed blindly. They hire people who can think independently, come up with appropriate solutions to problems and implement those solutions in ways that are beneficial to the organizations they run. Powerful people usually embrace thinking outside of the box - they do it themselves constantly - so as long as the end objective can be achieved, they will see the benefit for what it is and appreciate the ability to think creatively and achieve the desired end result.

Engage powerful people directly

I once witnessed the breakdown of a relationship between two individuals -- one a powerful leader and the other a person with incredible technical expertise in a support function. The leader became frustrated with the technical expert, not because of advice that he disagreed with, but because he felt insulted that he had been disrespected by a rejection of his proposed approach through email rather than a direct conversation. As the technical leader was my direct report, I discussed the issue in great detail with the leader, slowly peeling back layers of the onion to determine how interactions between the two had evolved over a significant period of time. The leader believed that whenever the technical expert disagreed with an approach that had been suggested by the leader or his team, an email interaction would occur, whereas when there was agreement on how to proceed, a face to face discussion or a phone call would occur. This had eventually come to infuriate the leader as he felt there should be more personal discussion on the difficult issues and less discussion on the easy ones. We often get busy in our day to day dealings and don’t spend the time needed to foster relationships. Indeed, the difficult discussions are the ones that people tend to shy away from the most. It is easier and “less confrontational” to fire off an email that says “here’s why we can’t do what you want to do” than scheduling a meeting or even having a phone call to hash out the details and engage with a powerful leader directly. However, those difficult situations can be the ones that provide the greatest opportunities: the chance to get involved in a situation in order to better understand a particular situation, obtain useful facts, and solve a problem; the chance to interact more with the powerful leader to better understand their perspective and the challenges they face; the chance to even develop a stronger bond with the powerful person through combined efforts in resolving issues.

Privacy is paramount

Given their positions and sometimes even their personalities, powerful people do not often disclose information readily to others without having a very good reason to do so. Information, no matter how small in detail, can often be viewed as power. However, once trust is established, a powerful person will sometimes disclose very personal details about themselves, family members, or even their own very personal thoughts and feelings. As a lawyer and eventually the company’s highest legal officer, I was highly trusted by numerous people who constantly disclosed business critical, important, confidential or even personal information to me. While it would no doubt be tempting for some recipients to share this information with others, that should be avoided for a number of reasons. It erodes the relationship of trust, even if the powerful person never learns of the disclosure. As a recipient, you know whether you can be trusted or not so such disclosures will impact your opinion of yourself. Further, disclosing information to others proves to them that you cannot be trusted. Over my career I witnessed numerous accounts of information being shared where the powerful leader ultimately learned of this disclosure through other channels. In some instances, it even led to the powerful person confronting the discloser directly as the powerful person knew that information had only been provided directly to that one individual. Not only can that be hurtful to the powerful person, but it can lead to the termination of strong partnerships. Indeed, for lawyers it can also constitute a breach of professional obligations.

Get personally involved in delicate issues

In my corporate role I ultimately became responsible for a number of global functions, one of which was Global Security. After the events of 9/11, when Osama bin Laden was still alive and evading the US, one of my company’s sales people located in India travelled into Pakistan and was arrested by the military for being in an area that was prohibited to foreign visitors. It was well known at that time that there was a great amount of distrust between Pakistan and India, so the very presence of an Indian citizen visiting Pakistan was enough of a concern for the military. Compounding the situation was the fact that our sales person had for some unknown reason been in close proximity to an election rally to support the ruling President, who was in attendance at the time, which obviously heightened the military’s concern. The individual was arrested, detained and interrogated. Many of our people attempted to seek his release but to no avail. As the General Counsel and the leader of the Security function, I was asked by the President of Sales to fly to Pakistan and negotiate the release of the Indian sales person directly with the Pakistani government. I travelled to Pakistan, met with the military, and with the Inter-Services Intelligence agency, the group responsible for gathering, processing and analyzing national security information. The Pakistani ISI is the equivalent of the Canadian Security Intelligence Service (“CSIS”) or the Central Intelligence Agency (“CIA”) in the US, and their involvement made it clear that the sales person capture was a national security concern. Eventually we were able to secure the release and safe return of the Indian sales person, but I was often asked why I had put myself in a situation of physically travelling to Pakistan to negotiate the sales person’s release when I could have negotiated by phone or correspondence or delegated to others including Canadian political authorities. Before I left, many people suggested to me that I should simply decline. Indeed, the CEO of the company informed me that I need not go if I did not wish to put myself in that situation. I immediately said I would go. My rationale at the time, which I still stand by today, was that as the leader of the Global Security function, if I abandoned one of our team members in their greatest time of need, and was not willing to look people in the eye in order to negotiate his release directly, then I was not fit to head the Security function at all, and perhaps not even represent the company as its General Counsel. There will likely come a time for almost anyone dealing with important issues involving powerful people, when you have to make a decision about how invested you are and whether you are willing to throw yourself into the heart of the matter, especially when powerful people are involved. I know that I always would have questioned myself had I not been directly involved and been able to negotiate with the Pakistani authorities face to face. I also wonder whether our sales person would have been released if someone had not personally advocated on his behalf.

Allow your personality to show

While it may be intimidating at times to even talk to a powerful person, they are still people, not robots and generally do not expect others to act like robots either. For the most part, powerful people wish to see the people around them acting in very real and human ways, displaying a sense of humour, empathy, and a wide range of emotions that would be appropriate in varying situations. While obviously that does not mean delivering an inappropriate joke in the middle of an important Board or executive team meeting, it does mean showing some of your personality in the right circumstances. What that means for each person varies depending on their type of personality, the role they have, the culture within the organization and the circumstances at any particular event. Depending on the organization you work at and the established culture, certain things may be more appropriate than others, so no matter what don’t try to be someone you’re not. When telling jokes for instance, there is a time and place for everything. Powerful leaders will often appreciate the timing of an injection of appropriate humour. If you get it right, humour can diffuse tension and put people at ease. Get it wrong though and you will certainly leave an impression, just not a good one for you! Above all, stay appropriate. I recall a corporate holiday dinner where significant others were invited. During the evening one of the CEO’s direct reports became intoxicated and picked food directly off the dinner plate belonging to the CEO’s spouse. Needless to say, the CEO was not impressed and the executive never made it to the next event as he was summarily dismissed from the company within months.

Final thought

When I reflect over my years at various organizations, I cannot help but think back on the numerous times I interacted with many different powerful personality types in various settings and circumstances. While there is no doubt that many of those interactions were initially intimidating, they also presented opportunities that helped further my career and the direction I took professionally. The experiences I had and the lessons I learned from those interactions, were beneficial to me in so many ways, not just professionally. Indeed, upon reflection, those lessons ultimately formed the basis of how I try to lead my life on a personal level today.

Michael P.J. McKendry is a recently retired executive with almost 30 years of diverse legal and business experience within multinational corporations and a large law firm. He has experience in a number of sectors including advanced industrial manufacturing, plastics processing, consumer packaged goods, food and beverages, home care products, as well as private practice. He currently is a Board member, investor and consultant. Michael can be reached at

Please note that the views and opinions expressed in this blog are those of the author(s) and do not necessarily reflect the views or position of Jenoir® International As we are critically-thinking human beings, these views are always subject to change, revision, and rethinking at any time. The authors and Jenoir® International are not to be held responsible for misuse, reuse, recycled and cited and/or uncited copies of content within this blog by others.