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Leading IT: Lessons from the front line

As a CIO, whatever challenges you face in terms of budget, mandates or timetable, you may already have the right people to carry out incredible IT feats. Here are four ways to lead your organisation to unprecedented success

If you’re an IT leader, you have one of the most distinctly demanding jobs of our time. From constant security threats to skills shortages, over-committed budgets, and lingering legacy issues, you face a full range of risks and competing priorities every day. At the same time, you also have incredible opportunities to create a lasting transformation in what people can accomplish. 

Whatever your IT portfolio includes, it may seem that more money, time and talent could solve your most daunting problems. Unfortunately, these fundamental resources are always limited – whether your organisation is entrepreneurial, governmental or sustaining the operations of a global corporation. 

There is never enough money, time or talent to handle the potential workload. The pressure to do more with less is something IT executives experience across the board. A significant aspect of your job is to figure out how to succeed within the constraints you’ve been dealt. I have discovered that the best way to do this is by leveraging the most critical factor in any organisation’s success: leading your people.  

You are in charge of getting the most out of your technology, systems, processes and – this is the key – your people. Your human capital is what will make the most profound difference in tackling huge challenges and achieving results that no one thought possible. 

I’ve had opportunities throughout my career to learn from exceptional people, including bosses, employees, leadership experts and peers. Over time, they have helped me to understand and develop the sensibilities required to succeed as a leader, no matter how complex or unprecedented the challenge may be. 

After a long career in IT, across industries including aerospace and finance, I became chief technology officer (CTO) and CIO at the US Internal Revenue Service (IRS).

I anticipated there would be plenty of legacy issues to navigate, along with the other limitations one would expect within a government agency. And that’s what I found.

“I believed that the very best efforts and ideas of my own people could unleash the awesome promise of our information technology”
Terry Milholland, TVM Consulting LLC

In addition to underperforming on a long-running modernisation effort, the IRS was under great pressure to transform the electronic processing of taxpayer returns to a database environment.

There were also new demands to migrate taxpayer requests online, prevent fraudulent payments and deal with unfunded Congressional mandates. Our budget was extremely tight, the filing season window was limited, and expert people were ageing and leaving the workforce.  

Even with these challenges, I had an insight. I knew that bridging the chasm – from where we were to where we needed to be – would require galvanising people around the tremendous possibilities for our future. If we could do that, we could dramatically change the predictable trajectory of false starts, late deliveries and cancelled programmes.

The key would be tapping into the latent reservoir of human spirit and skills I saw right in front of me. I believed that the very best efforts and ideas of my own people could unleash the awesome promise of our information technology. 

Whatever challenges you may face in terms of budget, mandates or timetable, it’s quite possible that you already have the right people poised to carry out incredible IT feats. With that as a starting point, whether you are in the public or private sector, there are four things I can share about leading your organisation to unprecedented success.

Listen and build trust

To transform what is possible, a leader has to truly listen and gain insight into their people’s reality as they see it. Why? Because that reality is the limit on action and performance.

Few of us appreciate the impact of perception on the amount of energy and emotion people are willing to invest in their efforts at work. Past disappointments can provide more than enough “evidence” for someone to conclude that giving their all simply isn’t worth the risk. Opting for lower expectations often seems like a far more sensible, less stressful way to decide what can – and can’t – be achieved. 

One of the first things I learned to focus on as a leader was listening to people. Really listening. At the IRS and in private enterprise, it was important for me to fully understand how people’s past experiences might influence the present. 

To get your people’s attention with a forward-looking agenda, they need to know that you understand their views on the consequences of past decisions, disappointments or failures, as well as what they consider the team’s strengths and past successes to be.

As you listen, you must be sure they know you heard it all: the good, the bad and the ugly. Revisiting the reasons behind any lingering frustration or fatigue may feel like a backward step, but it’s a necessary precursor to hearing about their hopes and dreams. When people see that you have absorbed their perspective on what is working and what isn’t, they will begin to take interest in the possible future as you see it.

Declare what’s possible

I’ve never seen an unprecedented achievement occur without the top leader first articulating it as an aspirational goal. This requires the courage to take a stand and declare what you believe your people can achieve. For me at the IRS, this was declaring that we would become a world-class IT organisation and beginning to act as if we already were one. Even if people don’t believe you at first, you must not back down. As they begin to rack up wins and results, that will change. 

This is the right time to identify and act on very specific possibilities for progress – solving problems, delivering enhancements – the very things that will make life better for the broader organisation. That’s the way the narrative will begin to turn from reasons why “it can’t be done” to reasons why “it might just be possible”. 

As you work to transform performance, you may meet with real scepticism. I certainly did when I told everyone on my IRS team that we could meet formidable breakthrough targets in the coming weeks and months. But just a year later, as we implemented new worldwide data security standards and ensured secure and advanced operations across the US, doubts began shifting to optimism. We were indeed beginning to operate at a world-class level.

It’s best to begin with small steps that show measurable progress towards the larger goals you’ve declared. As you do so, “asking” becomes a more powerful tool than “telling”. Rather than say, “We’re going to do portfolio management”, you could ask, “What applications do we have?”, “How many people are working on them?”, “What are we spending on them?”, “If you could do only one investment, which one would it be?”.

These questions actually begin the work of portfolio management. It’s a different conversation: they’re answering, you’re listening, and you’re moving ahead together. 

Pro tip for an IT renaissance: All eyes on the road ahead

Rather than focus too much on the most recent roadblock, keep everyone looking forward and thinking about what’s possible, rather than what’s not. This is an approach I first learned working with leadership experts at JMW, and it can generate momentum and extraordinary results. One key step is getting rid of silos.

While it’s not easy, you can do it by identifying and eliminating conversations that lead to distrust and inhibit collaboration. Taking ownership of a dysfunctional relationship or a devolving situation can be tough, but is well worth the effort. An open exchange of candid feedback from all parties can reveal the core issue and result in new possibilities for an innovative solution.

Applying these practices at the IRS resulted in a tectonic shift for our IT organisation: from a team mired in silos and past failures to a reinvigorated force within the agency. With unwavering aspiration and constant focus on the future, there are no limits to what is possible. You can unleash your people’s collective talent and commitment to deliver world-class levels of performance and results.

Yet making a bold declaration carries great responsibility. There will be times when the gaps are more evident than progress. It may often seem that your team’s performance is under scrutiny, and key players could feel their roles are at risk. Some people may revert to old habits that include negative attitudes and behaviours. You may find yourself hard-pressed to stay on course, on message and on schedule. 

That’s when it’s even more vital to shift their attention to the work at hand rather than focus on what’s wrong and who’s at fault. Ask questions that help establish clarity about where things stand: What’s been done? What hasn’t? Use the facts to set new targets that, when met, can recover momentum and demonstrate progress. Whether it’s week by week, month over month, or year over year, delivering measurable gains will get you back on track. 

Make decisions and move forward 

Part of leadership is taking on the right fight at the right time. Do you have a big overhaul to implement, but your email server is always glitchy? Get the email fixed first, then quickly pivot to the systemic upgrade.

As the pressure to deliver ratchets up, your people want to know you will stand with them through thick and thin. This requires courage and ownership on your part. Never blame the people who work for you. When things go wrong, hold yourself accountable with your key stakeholders.

“Use the facts and data you have now to make decisions quickly. Then move forward to the next situation. Avoid analysis paralysis”
Terry Milholland, TVM Consulting LLC

There will be inflection points where tough calls will be required to back up your teams. You may have to reallocate resources to offer more support, or even reassign personnel who are resisting the mission and putting a drag on momentum. Managing these kinds of adjustments without undue deliberation will save time, trouble and money in the long run.

Use the facts and data you have now to make decisions quickly. Then move forward to the next situation. Avoid analysis paralysis. Looking back, it was often the case that I could have acted sooner than I did. 

You will have to deal with constantly shifting priorities. Often these are due to factors out of your control, such as changing technologies and heightened expectations. The best decision one day or week won’t necessarily be the right call the next day or week.

What mattered to me as a leader was that care was being taken to keep work on track, with everything moving in the right direction. If your people know they can count on you to empower them – and their choices – they are much more likely to maintain their focus, energy and productivity.

Execute relentlessly

Try not to miss a beat as you oversee implementation, especially when you face obstacles. There may be ever-changing fixes and protocols to keep track of, possibly compounded by budget complications or personnel changes. As frustrating as they may be, these things are to be expected. You must persist and must not let up. 

For a leader, nothing escapes notice. As people see you operating calmly without getting overly distracted by issues that arise, they will do the same. When something goes wrong – inevitably, things do go wrong – remember that your reaction matters. Don’t treat it as a disaster or fly off the handle. Panic is the enemy of focus and effectiveness.

Another fundamental aspect of this work is communication. The listening and talking never stops. To remain effective, it always needs attention. Consistent avenues for inquiries, feedback and reporting across layers of the organisation, as well as vertically, are essential. 

Fine-tune your radar for signs of “business as usual”. Any pretense of alignment – “Everything’s fine, we’re all on the same page” – is often a conspicuous indicator of what will prove to be a significant disconnect at a later, more critical stage.  

You can start right now

Engaging people in a way that opens their hearts and minds to new possibilities for teamwork and accomplishment is a uniquely powerful, rewarding experience for everyone involved. The results of the breakthroughs you deliver can change the very future of your organisation.

Careers can be transformed. Organisations can be elevated to world-class. You might even spark an IT renaissance. It is possible, if you make the decision to lead your people there.  

Read more about IT leadership

  • NHS Business Services Authority chief digital officer Darren Curry talks about using technology to change people’s lives, developing accessible services and transforming the health service.
  • Harvey Nash’s CIO practice director shares her prediction on CIO trends for 2019, which include a growing demand for new technology skills, innovation and customer-focused initiatives. 
  • Where is the best place to be an IT professional in the UK? Computer Weekly looks at which location comes out on top for tech companies, and it’s not Silicon Roundabout. 

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