IT leaders can spend decades becoming experts at technology, systems, and processes, only to find that the move into the executive suite demands a very different set of skills. Leading a team is one thing. Having the presence and confidence to influence an entire business is another.

Barb Dossetter has seen that shift from several sides of the table.

Her career began in Australia, where she studied and worked across the major IT roles of the time. Her last responsibility there was running the first ERP implementation practice in the world across Asia Pacific. The role took her into different countries and brought her together with people from very different backgrounds and cultures. It also gave her a lasting connection with Singapore.

She enjoyed that part of the work so much that it stayed with her. After reaching the top job in her profession in Australia and Asia Pacific, she decided to take her career overseas. She thought she would be away for a few years. Then Europe brought exciting opportunities, followed by the US, and those few years quietly turned into a much longer adventure.

When she returned to Singapore in 2014, Barb continued working with her colleagues on one-to-one Executive Coaching and Group Senior Leadership coaching. Their experience of IT leaders demonstrated that many with an Insight colour of blue are analytical, objective, and detached and are losing out on promotions. More ‘soft skills’ are needed for a successful executive.

That understanding became part of how Barb and her colleagues approached coaching. They began calling it coach-mentoring, combining guidance with the practical support senior leaders often need as they prepare for their next role.

The work eventually led to the Global CIO Leadership Certification Programme, which they have developed and delivered for the past five years. The programme helps IT leaders develop the presence needed for the executive suite and prepares them for life as CIOs.

For Barb, it is a natural continuation of a career that started in technology and grew through people, cultures and leadership. She once crossed borders to find the next challenge in her own career. Today, she helps other IT leaders prepare for theirs.

Barb has been inspired by two ‘pro bono’ roles she has taken up in Singapore. She is on the SCS Supply Chain Management Chapter Executive Committee and is a judge on the Women of the Future ASEAN, which recognises women’s courage and inspirational leadership. Both have taught her much about people in the region.

From Research to Real Conversations

Senior executives often begin by looking for information, but the real challenge comes when they have to decide what to do with it. Barb saw this shift early in her work with clients, when research alone was no longer enough, and leaders wanted someone to help them work through their own situations.

While there had always been a degree of coaching in her interaction with clients, this became a key part of her work at Gartner with the Best Practices Councils at the time across Europe. Clients did not just want to read the research; they wanted to discuss it.

Those discussions quickly morphed into coaching conversations about how they wanted to implement solutions. The conversations were not about giving them answers but working through their situations and discussing alternative solutions with them.

When Barb joined CIO Connect in the UK, the work moved further in the coaching direction because they believed then and now that their role was to help the executive define the right solution and identify the path to achieve their objective.

Understanding the Person Behind the Role

A CEO, CIO, or CMO can sit around the same table discussing technology strategy while approaching the subject from very different pressures and perspectives. Barb has found that understanding those differences is essential to making an advisory relationship useful.

She shares a little secret. Often a CEO will discuss strategy and technology strategy more openly with an external coach like themselves because they are not a risk to their professional reputation or their self-image.

That is why the coach must understand corporate strategy and technology. Barb and her colleagues often “teach” the CEO about the technology and its implications across the organisation. The CIO usually has the same conversation, with the CEO seeking external advice and validation. Usually, her advice backs what the CIO has been saying.

Regardless of the CXO role, Barb believes it is important to understand how the client thinks and communicates. The coach needs to understand their role and the challenges they have. They also need to understand what drives them, what their professional KPIs are, and what their personal wins or important issues might be.

The same conversation about the same subject can happen in different ways because of how clients take in and process information.

There is another part of the relationship that is easy to overlook. However senior the client is, they are still a person. Barb believes the coach needs to help them understand themselves better so they can be successful.

What Technology Transformations Reveal

Understanding people becomes even more important when the stakes rise. After working on more than 500 ERP systems across three continents, Barb has seen what happens when large technology programmes encounter organisational realities that cannot be solved by technical competence alone.

Unfortunately, she believes organisations are still no better at doing this now than they were decades ago.

The issues that cause difficulties and failures are people related and, often, communication rather than competence.

If a project starts with unclear objectives, a lack of enthusiastic executive sponsorship, disengaged business colleagues, and a failure to manage the Systems Integrator, the consequences can be serious.

At best, the project will cost more and take longer. At worst, it will fail outright and may bring the organisation down.

For Barb, the key leadership characteristic is having the courage to speak truth to power.

How Culture Changes the Conversation

The willingness to seek that kind of outside perspective varies across regions. Barb’s experience in APAC, Europe, and North America has shown her that geography can influence how executives approach coaching, while other factors can matter just as much.

She thinks that a European or North American executive is more likely to initiate coaching than someone from ASEAN. Gender creates another dynamic. Men are more likely to ask for coaching than women.

In Asia Pacific, most of Barb’s clients come from multinational companies headquartered in Europe or North America. She believes that seems to give local executives permission to access coaching themselves, especially group coaching.

Executive coaching and advisory work are also difficult to separate completely. Barb and her colleagues are often brought in as advisors to address a problem. As they work with individuals, the engagement can then morph into executive coaching as they help people grow into the new requirements of their roles.

Turning Technology Hype into Business Value

Technology can attract attention long before an organisation has established whether it actually needs it. Barb’s approach starts by slowing down the conversation enough to separate what is genuinely useful from what is simply attracting attention.

She calls the first step Reality Check.

Firstly, she believes they need to agree on what is different about the technology under discussion.

According to Gartner, Agentic AI is in “inflated expectations” of the hype cycle. As a neutral, vendor-agnostic group of people, Barb and her colleagues can work with executives to reduce the hype and discuss the reality, good and bad.

They are often the only truly product-neutral people that executives talk to. They do not have a huge consulting practice to feed, nor tools to sell.

The next question is Business Need.

Given the state of fit-for-purpose technology, which business processes, from customer-facing to back office, would benefit from redesign? What is the likely payback? Who should be involved in the discussions, and what will they bring?

From there, Barb looks at the key components of success: People, Process, Data, and Technology.

Companies also need to identify how they are going to learn the new technology in-house so they do not leave their destiny to outsiders.

Then comes Execution Support: providing an external voice that raises questions that may not be being addressed.

Getting to the Point

The ability to communicate all of this effectively matters, particularly when the audience consists of executives who have limited time and little patience for presentations that take too long to reach the point.

Barb’s advice is simple: “Don’t be boring.”

C-level executives are time-poor. Speakers need to know the audience and what they care about. They need to do the research and check their assumptions early in the presentation.

“Don’t waste their time.” Getting to the heart of the matter quickly is important.

If there is a flavour of the month or year, such as AI, it becomes part of the conversation.

Barb also encourages speakers to be original and leave the audience with three things or takeaways to consider as their last thought.

Questioning the Innovation Rush

The same discipline applies when executives are deciding whether to invest in a new technology. Innovation can create its own momentum, and Barb often sees decisions being made emotionally and then facts are gathered to support them.

Her response is to ask some very basic questions.

People can layer solution on solution without realising that they have built a very big house when a cabin on the coast would have been sufficient.

She sees this happening with AI now as people say AI is the answer before they have decided on the question.

“Often, it’s a bandage on a fractured process.”

There are likely to be all sorts of motivations behind the innovation decision, whether the answer is to go or no go. They need to be identified and understood. People need to be heard if they are to collaborate. An honest and confidential conversation can make those motivations visible. Barb wants everyone to understand the implications of the innovation decisions in front of them.

She also looks at the WiiFM for each of the recommenders: “What’s in it For Me”.

Walking through the risks and the risk reductions, even at a high level of discussion, helps determine the balance.

When a Business Needs to Turn Around

A struggling company creates a different kind of pressure. The leadership team has to move quickly, but Barb believes the early steps need to establish support, direction, and a clear understanding of what the organisation is trying to achieve.

The first step is to get the investors and the board on side to support what the leadership team wants to do. This will be the CEO’s role.

The second thing that Barb and her teams did in the past was determine who the customer was and what they wanted from the organisation. They turned that into a vision and mission and made sure everyone was behind it.

The process needs to engage the executive team, and some invited others. Engaging the senior leadership team is the critical lever.

The next step is to develop the plan, including the communication to staff and the external communication plan if needed.

Every leader should also be coached on how to talk about the plan with conviction and honesty, including some of the nasty bits that may need to happen.

Deciding What Comes First

Once a business has direction, executives still have to decide where their limited time and resources should go. With competing projects, urgent requests, and long-term objectives all sitting on the table, prioritisation cannot be left to whoever argues most strongly for their initiative.

Prioritisation is an annual planning activity for executives, and Barb believes it is better done as a group activity, with guidelines set by the CEO around the organisation’s objectives for the following year. Reprioritisation during the year may be necessary as the business environment changes.

Helping the CEO articulate those guidelines is often done with the external coach.

The business needs to own the prioritisation.

For a CIO, a CFO or a CPO, Barb’s role is to coach them into the “trusted advisor” space rather than the decision-maker position for business projects.

Learning From Other Leaders

Senior leadership can become an isolated position, particularly when executives are surrounded by people who report to them or depend on their decisions. Barb encourages her clients to build relationships beyond their immediate organisations.

She encourages clients to network to build their professional brands and learn from others.

Sometimes, finding the right people is the challenge.

Before an ERP Programme Begins

The early decisions around a major ERP or CRM implementation can determine how difficult the programme becomes later. For Barb, one condition is important enough to establish before the project begins.

“Don’t start unless you have an active Business Executive Sponsor and an engaged business group who commits the time and subject matter expertise.”

The Future of Executive Coaching

AI is already changing how executives access information, analyse problems, and seek advice. Barb expects that to influence coaching too, particularly as AI becomes capable of providing forms of guidance that once depended entirely on experienced professionals.

It is easy to see how AI advice may well take over the advice of experienced coaches.

But Barb believes there are parts of executive roles that are physical and need to be integrated into the whole person.

For her, effective coaching requires the willingness to challenge the client rather than simply support whatever they are doing.

A good coach who wants the client to be successful will also call out the client when their performance is sub-par.

The role will change. Coaches who have less to offer their clients will probably lose out.