HomeSocial Impact HeroesOliver Shaw Of Orgvue On How Leaders Make Difficult Decisions

Oliver Shaw Of Orgvue On How Leaders Make Difficult Decisions

An interview with Maria Angelova

Remain calm in the face of uncertainty and give yourself time to think.

As a leader, some things are just unavoidable. Being faced with hard choices is one of them. Leadership often entails making difficult decisions or hard choices between two apparently good paths. What’s the best way to go about this? Is there a “toolkit” or a skill set to help leaders sort out their feelings and make the best possible decisions? As part of our series about “How Leaders Make Difficult Decisions,” we had the pleasure of interviewing Oliver Shaw.

Oliver Shaw is an experienced leader of fast-paced, sales-led organizations across numerous products, industries, and distribution channels. He has a strong track record in delivering shareholder value by executing strategies that drive growth in revenue and profit, while delivering world-class service to customers.

Oliver began his career in sales and marketing roles in consumer financial services, helping to build fast-growth brands like Capital One and Ageas Insurance. He moved into the technology sector in 2009 when he joined IRIS Software. He has spent the last 10 years in executive roles including Divisional CEO and Merger & Acquisition Director, helping to build one of the largest privately owned software companies in the UK with a valuation in excess of £1 billion.

Oliver joined Orgvue as Chief Executive Officer in January 2023 from retail analytics platform, Kalibrate. He holds a degree in Business Studies from Humberside University and an MBA from Nottingham Trent University.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

From early on in my career, I was fascinated with finding ways to make business processes work better. My first job as a process analyst gave me a really good insight into how a business functions across departments. At the time, I was studying part-time for my MBA, which set me up with a good understanding of the fundamentals.

I then spent a few years working on project management, where I helped build IT systems and manage workflows. As a result of this, I secured a new role in my mid-twenties working for a fast-growing financial services company from the US that had entered the UK market. The role was in growth opportunities, which was a separate unit to the main business.

I was brought in to build a billing system for a telecommunications organization. The business wasn’t operating well commercially and I saw an opportunity to fix that. My instincts told me that, despite having no sales experience, what I did have was a track record in getting things done, a solid understanding of how businesses work, and a go-getter attitude. By finding the confidence to lead on this project, my career took quite a turn and I ended up taking a role as Commercial Business Leader.

Quite quickly, I was running inbound sales campaigns for the bank. And then, a couple of years later, I ended up as the Sales and Marketing Director of an insurance company, running very large outbound call centers. While I was in that role, we saw an opportunity to build another business targeted at the over 50s, which went from 300,000 policyholders to 2.5 million policyholders in four years. Then in 2008, I made the decision to move out of financial services and into tech, and that set me down the path to where I am today.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?

I’ve sought out different relationships and sponsors throughout my career as I’ve changed job roles and moved industries. There are a multitude of stories I could share, but a moment that stands out for me is back when I was starting my career. At twenty-one, I worked in a sales office as part of my University placement year. The guy who ran the office took me out for lunch, and as many of us are at that age, I felt self-conscious and lacked confidence.

He sat me down and said “it’s really important that you believe you can go as far as you want in your career. You’re a clever guy, you’re honest, and you work hard; you’ve got all the qualities you need to be a successful leader.” No one in education had said that to me before and it gave me the confidence to push on hard in my career.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

Over the past fifteen years, I’ve managed more than ten different business units or companies, at different levels of maturity, capability, and performance. One that stands out was when I’d agreed to sit in on a business review meeting during my first month, and it literally collapsed in front of my eyes. Someone left in tears and the interim managing director asked me to run the rest of the meeting despite being new — it was bad. The best thing I did in this situation was to stay calm, even though I felt wholly unprepared for this responsibility.

If you’re the leader, everyone is watching you. As soon as you show you’re feeling the pressure, a degree of uncertainty will trickle down to everyone else. Whatever stress you feel, whatever concerns you have, whatever challenges you face, as a leader you have to deal with them privately. I’m not saying you should bottle up stress and deal with it alone, but find the right time and place to deal with your emotions, so they don’t have a negative knock-on effect. This could mean finding a mentor that you can have that type of conversation with. So that’s number one, remain calm, keep your own counsel and stay focused.

The second most important thing is to have mental clarity. You need to be clear on what the two or three essential things are to keep sight of. To support that, give yourself more control by shortening management cycles. If you have one-to-one meetings every two weeks with your direct reports, make them once a week. If you have management meetings once a quarter, make it once a month.

One of the most powerful things a leader can do is accept that they don’t know everything, and that’s okay. But what’s crucially important is that you think and do simultaneously. What makes a good leader is someone who’s willing to accept that success is often the result of overcoming many obstacles.

Did you ever consider giving up? Where did you get the motivation to continue through challenges? What sustains your drive?

Sometimes, giving up could be a good strategy and it’s always an option leaders should consider. Tenacity has value but not always; there’s also value in knowing when you need to “change the game”. There’s no point beating your head against a wall that isn’t going to move.

Nobody should think that stopping and giving up in a toxic environment is a weak decision because it’s the opposite. Stopping and changing direction means thinking about the strategy you’re following, understanding where the value is, and where there’s room for growth. Motivation can come from facing reality, because you hold the power to change the game and influence positive business outcomes.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

Over the years, I’ve been in situations with a lot of operational challenges and I’ve had to deal with redundancies in tough economic conditions. As a leader, sometimes you’ll have many ‘good’ paths available and other times it’ll seem you have none. Whatever the situation, I’m always diligent in my decision-making process. This means running through the available options, checking decisions against data, and committing to the decision that’s best at that moment in time.

What process or toolset can a leader use to make a choice between two difficult paths?

I had a coach for a period of time. He was an ex-marine and he told me a story once. When things are chaotic and it’s unclear which path to take, the way you deal with it is to move towards the problem. That’s also what firefighters are trained to do — run towards the fire. The reason for this is that you’ll get ‘feedback’ from the situation that will allow you to correct your approach. If you stay where you are, you die, or in the case of firefighters, someone else might; stagnation is simply not an option. The same is true in business today.

The main lesson to take away from this is that, in the most challenging situations, you just have to do something. There’s almost always the option to adapt, but it’s having the authority and confidence to commit to a decision and move forward that’s important. This sets the tone for progression and success.

Do you have a mentor or someone you can turn to for support and advice? How does this help? When can a mentor be helpful? When is this not helpful?

This is something that varies from person to person, but in my experience, yes, a mentor can be immensely helpful. Particularly in the early stages of your career when you’re developing your confidence and defining your leadership style.

What would you say is the most critical role of a leader when faced with a difficult decision?

The most critical thing is to set the tone. If you start running around like a headless chicken, that’s what everyone else will do. However you feel, your job is to help everyone else get to the right place. I talk about this idea of having a long shadow and that shadow is all the people that work for you. You have to bring them with you and deliver them to the right outcome.

When you’re thinking about difficult decisions and how it’s going to impact your team, help people understand your logic and the process of how you arrived at those decisions. Most importantly, set a tone of calmness, because if uncertainty is affecting your employees, or even your customers, think about how this make them feel. Approach all difficult decisions with kindness, dignity, and justification.

Do you ever look back at your decisions and wish you had done things differently? How can a leader remain positive and motivated despite past mistakes?

You should be assessing your decisions continuously. Embrace the fact that mistakes will happen and that you’re in control of adapting your strategy. The variable in that control is time. The more time you can create between the inflexion point — when you have to act and get a result — and the point you’re at, the better, because you’ll be able to consider more of the options that are on the table for what you want to achieve.

There have certainly been moments in my career when time hasn’t been on my side and I’ve not had enough information to lead me to a clear decision. It’s in these moments that my leadership qualities have been tested and again it comes back to being calm, decisive, and committed to moving forward. Mistakes are inevitable but the best leaders will embrace them as an opportunity to enhance their leadership.

What is the best way to boost morale when the future seems uncertain? What can a leader do to inspire, motivate and engage their team during uncertain times?

When things feel uncertain, it’s crucial to communicate regularly with your team and create calm amid the chaos. It’s understandable that morale may be less than you’d like at times like these, but leaders should not overlook the power they have to influence the culture of the business.

Anita Roddick of the Body Shop, a very accomplished leader in my view, worked out early on in her career that the most important thing she could tell her employees when she met them was that they were doing a great job. This may sound simple, but people feel motivated by praise, and a simple act of recognition can go a long way to maintaining a positive company culture.

Can you share 3 or 4 of the most common mistakes you have seen other businesses or leaders make when faced with a hard decision? What should one keep in mind to avoid that?

Despite advances in technology and the availability of organizational planning software, the most common mistake I see business leaders make is deviating from their strategic plan during times of chaos. Planning gives leaders the ability to forecast and define the best possible course of action in a given set of circumstances.

It can be tempting to change strategy when faced with tough decisions, but I think a good leader will always turn to data to validate the decisions that they’re about to make. Snap decisions are often made when leaders are led by their emotions and, in my experience, they invariably come to regret those decisions.

In a research study we did recently, most business leaders admit to making snap decisions, many of which led to unforeseen organizational outcomes they later regretted. These were the headline stats that came out of the research:

  • 93% of senior decision makers at large organizations say they’ve made a short-term or quick decision with cost cutting in mind, with more than a third (38%) later regretting it.
  • Almost two-thirds (60%) admit these same decisions were later viewed negatively by the organization.
  • A quarter (24%) lost valuable talent that they later realized they needed.

Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a leader should do when making difficult decisions?

1 . Understand your decision-making process in specific detail.

2 . Use data to validate the decisions you’re about to make.

3 . Communicate your logic to the people around you.

4 . Remain calm in the face of uncertainty and give yourself time to think.

5 . Own the outcomes you produce.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Panic early”. My view is that often there’s a temptation to let the chaos of the moment take over. Your adrenaline is high and you’re working under intense pressure. But if you find yourself in that situation, you’ve actually failed already.

What a good leader should do is anticipate the issues and prepare for what they will mean. There’s no point in lamenting your inadequate sales pipeline when you should have addressed the problem six months ago.

Always think ahead. The more time you can create between thinking about the problem and making the decision, the better the outcome will be. “Panic early” means taking the time to build adrenaline and tension around the plan early on, rather than being faced with the avoidable consequences and having your hand forced.

How can our readers further follow your work?

You can follow me on LinkedIn and keep up to date with our company news at

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.

Thank you for the amazing opportunity!

About The Interviewer: Maria Angelova, MBA is a disruptor, author, motivational speaker, body-mind expert, Pilates teacher and founder and CEO of Rebellious Intl. As a disruptor, Maria is on a mission to change the face of the wellness industry by shifting the self-care mindset for consumers and providers alike. As a mind-body coach, Maria’s superpower is alignment which helps clients create a strong body and a calm mind so they can live a life of freedom, happiness and fulfillment. Prior to founding Rebellious Intl, Maria was a Finance Director and a professional with 17+ years of progressive corporate experience in the Telecommunications, Finance, and Insurance industries. Born in Bulgaria, Maria moved to the United States in 1992. She graduated summa cum laude from both Georgia State University (MBA, Finance) and the University of Georgia (BBA, Finance). Maria’s favorite job is being a mom. Maria enjoys learning, coaching, creating authentic connections, working out, Latin dancing, traveling, and spending time with her tribe. To contact Maria, email her at [email protected]. To schedule a free consultation, click here.

Oliver Shaw Of Orgvue On How Leaders Make Difficult Decisions was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.