Beyond communication and advocacy, there's several skills, characteristics and capabilities that a CDO will need.
Let's look at each in turn.
So, we've established that communication is the key skill for a delivery principal followed closely by advocacy, which often looks like diplomacy. Beyond that, though, what other traits or abilities are important to lead customer delivery?
Here's a list of seven CDO super-powers, and we'll look at each below.
Building relationships #
The CDO needs to be a master at relationship building.
Most obviously, projects get done because people do them, and the better those people are connected to the focus and purpose of the task, the higher quality the outcomes. Consequently, fostering personal connection is a vital component of delivering stuff.
There's a wider view, though.
The CDO will need the support of peers in the C-suite to achieve the delivery strategy vision. You will need the help of others in the wider business to execute the delivery strategy effectively: the technical and/or design specialists who engage directly with customer needs; the business's support and success services for ongoing health of what's built for clients; sales and marketing for landing the right kind of customers, and for a coherent persona and customer experience from beginning to end; and so on.
Rapport is essential to nurture long and healthy relationships with customers, of course. You need to connect in order to see the world from their perspective, to understand their needs and the goals their aiming to achieve, and for the client to trust that you're focused on the right outcomes for them.
Occasionally, the CDO will need to go toe-to-toe with colleagues to advocate for things that are important or to achieve certain necessary ends. But the most effective results will be achieved through building strong and healthy interpersonal connections.
The power of cake #
It's astonishingly important to spend social time with people.
Taking time out to share a piece of cake, to have a coffee with a colleague, or breakfast, or if food's not your thing then going for a walk together — it's powerful.
Informal settings put everyone at ease, and vital to take time to talk informally, about wider topics — hopes and dreams, frustrations and challenges, personal stories of how we got here, what matters to us, what keeps us awake at night, and so on — to help build strong bonds.
It helps to understand what motivates people. It creates safety to talk about struggles or difficulties. It opens up new insights into ways that you can help.
Cake is powerful.
Building trust #
Clients and people in your own organisation, at all levels, alike will need to trust you. At times, they will need to have faith in you to make judgement calls.
Trust is especially important when taking on big or risky challenges with lots at stake.
Trust doesn't come from nowhere. It's not a switch to be just turned on.
It derives from consistency, honesty, and reliability, from behaving with empathy and consideration, and it requires transparency in actions and decisions.
In other words, the trust that a Chief Delivery Officer has to rely on means they must be a person of integrity.
Building respect #
Respect is reciprocal.
As you give respect — to your customer and the specialists in their team, and to your colleagues and peers in your own company, the experts you have around you — and both display and act with empathy and understanding to their situation and context, so you will be given respect in return.
In particular, this is about recognising expertise in other people.
As a CDO or a delivery lead of any kind, you do not need to be the fount of all knowledge, and it's not your job to determine what needs to be done.
Instead, your role is to facilitate a collaborative effort. You convene a group of capable and experienced people to pool their wisdom and their efforts together in order to reach a particular, shared outcome.
The heart of that is respect — the effectiveness of that collaborative venture is determined in large part by the high regard a team of people with great expertise show to each other.
Build respect, then, and you lay the ground to achieve great things.
Strategic vision, tactical view #
As with many aspects of the CDO role, being able to hold a creative tension between strategy and execution is a distinctive quality.
The role requires you to do both — to see far ahead, and determine how to get where you're going; and, to take one step at a time on the path you've set, without getting distracted or discouraged.
Or, to put it differently, it's about altitudes of thinking — taking the time to stand on higher ground to get the long view, whilst knowing that things are put into action back at ground level.
Strategy: Walk up the hill to see the horizon #
You'll be familiar, from your long experience of running customer projects, how important it is to start with a focus on the outcomes and to keep that focus all the way through. The same is true when working out how the business should be interacting with customers and delivering on its promises.
At ground level, things can appear quite suddenly and erratically, almost as if out of nowhere. That'll cause you big problems, as if you're always putting in effort just to stand still. And it's because your view is too short — the horizon is very close, where things can hit you without much warning.
You need to get to higher ground where the horizon is further out and your view is both longer and broader, taking in the landscape all around you.
From higher ground you'll have a clearer view of your objective, and of the lay of the land in between, the immovable objects that have to be dealt with, the rivers, forests, canyons, and so on. From this loftier view, you'll be able to work out the best path to get to your goal.
You'll also have a better perspective on things that are moving, the weather, the challenges or opposition that may impede you on your way, etc.
This drawn-out metaphor is what strategy is all about.
- Keep focused on the end-goal, on the outcome you want
- Take account of what's immovable in between
- Evaluate what's moving, and understand the risk it poses on your path
- Choose the optimum route to get to that destination
- Work out a plan for the journey you're going to take
- Test that plan as thoroughly as you can, so you're not unduly surprised
- Break the whole thing down into achievable steps
- Work out how you're going to know how you're getting on when your vision isn't as clear, when things get tough
- Put in place the team and the equipment you'll need along the way
You can only do all this if you take yourself off up the hill first.
Tactics: Ground work at ground level #
Lovely though the views are, you're static on the mountain top. The journey doesn't happen here.
To get stuff done you have to come back down to ground level.
If you've put in good planning time, then you'll have a clear step-by-step directions to follow. You'll definitely know the landmarks and way-points. But should know a lot more than that, something close to a turn-by-turn guide to follow.
One of the things you should have identified is the challenges and risks to your big venture. In your thorough planning, you'll have worked out how you're going to tackle particular obstacles, the bigger challenges you know are on your path ahead.
This is the definition of tactics, pretty much — how you're going to address specific things that are part of the larger plan, the distinct things you need to achieve or overcome in order to get where you're going.
Your tactics are the hard work you do at ground level, in the day to day. And your tactics are the reason why you've drawn together this specific the team and these particular tools — so that you can handle what you know is coming at you.
Beware of too much improvisation, too often #
Often the term 'tactics' is used as a synonym of 'improvise', but that's not really right. Yes, occasionally you will have to react, to be spontaneous. But if you're doing that too often then it's a strong clue that you didn't spend long enough at high altitude, that you were impatient.
If that's the case, you probably have a fundamental flaw to deal with.
Pause.
And go back up the hill.
Master for solving problems #
That said, problem-solving is a core constituent of delivery leadership, and excellent CDOs will be exceptional in this area. The skill is equally important when analysing your challenges and planning out how you'll address them as it is when needing to adapt to an obstruction on the fly.
Part of your credibility (discussed below in more depth) is your own pre-existing expertise in the organisation's industry, sector, and core business. You may also have important experience from a distinct specialism, data or design or engineering, say. You will undoubtedly lean on that history and long experience when tackling difficult problems — the pattern of thinking about problems that you've acquired over your career to date are transferable skills and will remain vital.
The problems you'll experience when building your delivery strategy and executing on it will be approached in the same way:
- define the problem;
- analyse it;
- generate solutions;
- evaluate them;
- select one (or two) as promising options;
- determine how you'll know it's a valid fix;
- try out your options;
- (depending on the scale, you may just skip straight on [small] or run a pilot [large])
- implement the best;
- measure the impact and make adjustments.
You know how it goes.
Catalyst for change #
If you're the first CDO the organisation has taken on, it's inevitable that you'll be the author of substantial change in the business. If you're a successor to a previous incumbent, change is still probably your watchword as you evaluate and revise — to whatever degree — the way the organisation delivers for its customers.
Enabling change depends on all of the dimensions discussed here.
In particular, it requires you to have strong and healthy working relationships with colleagues across the business — not only will they be a vital support for what you're aiming to do, but in certain areas you'll need direct help as you transform the things that need transforming.
It also leans heavily on your potent skills of communication, which we've already discussed at length — you'll need to be painting pictures about what you're changing, why you're changing it, how things will change, what that means for everyone, what difference it'll make and how it'll help, and so on, all the way through. Don't underestimate the need to communicate, and to keep on communicating, as you embed the transformation you're aiming for.
Of course, it won't all be plain sailing, and we'll talk about the quality of resilience below.
Think slow, act fast #
This is one of the key heuristics for delivery leadership that you'll already know well, but when doing stuff it's vital to take time up front to think things through thoroughly before you get on with implementing things.
You can boil all that down into a single phrase, coined by Bent Flyvbjerg, the project management guru and Professor of Major Program Management:
Think slow, act fast
See Flyberg's book, How Big Things Get Done for all the deep thinking behind this pithy phrase.
It's cheaper and quicker to find problems and see things fail when you're still planning your work. Reduce uncertainty with low-cost research, testing, prototyping, and then roll those insights into better planning.
Then, move quickly and deliver rapidly based on the thoroughgoing plans you've made. The longer you spend in the execution and the slower you move at this stage, the more space it gives for things being adapted — either needing to, or being forced to.
If change is foreseen or forced on you, then Agile methodologies are extremely helpful.
Structured thinking #
Strong organisational skills are one of the most important dimensions of your work as a CDO, and these are something that will have been a feature of your career all along, no doubt.
But organisational skills are functional skills that need to be focussed through a specific lens that we might call structured thinking — the ability to …
- tackle difficult things methodically,
- to analyse demands, needs, situations and more in a systematic manner, and
- to work with reasoning, likely with reference to a framework, towards usable solutions or outcomes.
Let's explore this in more depth.
Analytical #
The analytical mindset is about taking a set of information — whether succinct, such as business goals or client objectives, or loose and open, such as usage or performance data, or user needs from interviews, say — and performing several actions on it.
Analytical approaches then do two things.
First, they decompose that information into smaller elements, maybe even into constituent parts. Complex things are tackled more easily when they are broken into smaller pieces. Although the whole thing operates together as a unit, the effect of the whole is achieved by the traits and characteristics contributed by the components.
And secondly, analysis requires that individual significance AND the relative importance of each part is identified. What does each part do? Why is it important? And how should the effect of each be weighed in relation to the other parts?
Systematic #
Complex information then needs to be addressed in a logical manner, piece by piece.
Being systematic means that your analysis covers each element and gives it the attention it deserves. Being methodical allows you to be appropriately thorough.
Focused on usable processes #
As you construct processes, tools and practices for your business, it's essential that they sit aside from you as the CDO. They cannot, they must not depend on you to be implemented in practice.
Delivery processes need to be replicable by others in the business. Ideally, they should be usable by people who aren't delivery management specialists — designed to be used by non-specialists.
If a project or a customer needs to switch the project manager for any reason (illness, scale, personality, sector specialism, whatever) it should not feel like totally different delivery experience.
Credibility #
The art of building relationships discussed above is built in part on credibility.
A CDO must be credible to the CEO, the founder(s) and the board, their colleagues, the business as a whole, and vitally, to customers.
The business as a whole needs to be confident in the CDO, especially as they introduce (potentially) big ideas and significant changes — credibility is essential.
Credibility and knowledge #
A large degree of your credibility will be derived from specialist knowledge.
A new CDO will need to have a thorough understanding of delivery methodologies and frameworks, both theoretical and practical. And you need a thirst to learn more, to keep up with innovations in the field, reading articles and books, attending conferences, and so on. But that isn't enough.
Credibility also benefits from a good working knowledge of the field, sector, or specialism of the business. The better you understand the challenges and needs of the delivery teams you're overseeing, and the optimum working context of the experts in your teams, the better you are able to serve and support them. If you're leading digital engineering delivery work, for instance, then a background as an engineer, programmer, system admin, or similar is hugely advantageous. The same if it's a design business, a marketing agency, and so on.
In many cases, you will need to be a translator, between customer, business, and team. Each will need to feel they are represented, that you're not necessarily on anyone's 'side' in particular (see previously, on being the ultimate advocate) — you are on the side of outcomes … and those don't flourish in silos! You can only do that if your knowledge of the business's specialism is rock solid.
Credibility and authority #
High performance CDOs must have authority.
But the only true and valid authority derives from credibility. Authority is established through credibility, rather than the other way around.
Ideally, authority to effect change and implement practices that affect the whole business will be projected through clear support from above. But without credibility, that will quickly ring hollow.
Be consistent, stay focused — the credibility will build itself.
People-centric #
Delivery leadership is many things, but it is particularly people-centred.
You may be making sure customer's get what they're trying to achieve, overseeing processes and practices, setting standards and making sure they're maintained, and so on … but all of that involves people — your customers and their teams; everyone in your delivery teams; the wider business, the leadership, and other colleagues.
Especially high emotional intelligence (EQ) #
An essential quality of a high performing Chief Delivery Officer is that they have unusually high emotional intelligence — the ability to perceive, understand, and manage emotions in one's self and in others. It's what helps you to maintain composure under stress rather than jump off the deep end.
There's several reasons why high EQ is a vital trait for a CDO, some of which we've touched on above. In particular:
- The delivery process is, in part, an expression of the character of the business — it's your job to work out how to do that best
- You'll need to influence people with authenticity — so they follow your leadership, and so that you can effect change
- Things will get escalated to you — challenges in projects, with customers, amongst team members, etc. — and you'll need to handle and resolve these challenges
So, what does a high EQ look like? There's many characteristics of someone with high emotional intelligence, but here's 12 that should be at the forefront.
If you're a CDO already, these are probably things you'll recognise. If you're aspiring to a CDO role, these are traits for you to consider in particular. If you're looking to hire a CDO, these are qualities you should be looking out for in the appointment process:
- Self-awareness
Being highly aware of one's own emotions, behaviours, responses, triggers, and patterns, sensitive to one's emotional state at any given moment and able keep a check on one's self. - Self-knowledge
Reflecting on ourselves and our history leads to a deeper awareness of who we are as human beings, including our strengths, weaknesses, values, and level of integrity. This may uncover things we’d rather not acknowledge. - Self-effacing
Confident and standing up for opinions or principles, but recognising that you don’t know everything and being willing to learn from others, not seeking praise or requiring affirmation in order to pursue something. - Empathetic
Perceive, understand, and sense other people’s emotions, feelings, moods, and perspectives, requiring social awareness and reading social cues, body language, and other forms of communication. - Strong impulse control
An advanced trait that involves your ability to control, regulate, and manage your emotions, impulses, and behaviour. - Self-disciplined
Exerting control over trains of thought and mental states leading to self-regulation and discipline towards difficult tasks, goals, and long-term achievements. - Authentic
Someone who is open, genuine, and true to themselves, full of integrity such that they're the same person sliced in any direction. - Resilient
Someone who is difficult to offend, having a thicker skin than usual, who is aware of other people’s emotions and psychology, and understands when not to take things personally. - Adaptable
Adjusting well to changes, understanding how to respond to new environments, and can adapt their social approaches to suit other people’s needs. - Taking a moment to think
Able to pause, reflect, and compose one's self before reacting, being especially aware of emotional triggers. - Able to apologise
Courageous and confident enough to apologise, swallowing one's pride, with apologies that are sincere, heartfelt, and meaningful – not dismissive, fake, or filled with gaslighting. - Good with feedback
Feedback is tricky — both giving and receiving — yet also essential for success. It can be sensitive and personal, especially when talking about something difficult, and managing emotions is vital.
Cheerleader for people and initiatives #
A CDO is playing a team sport, and high performance teams play at their best when they have all the means necessary to be their best self.
Cheerleader for people #
An effective CDO is looking out for every person in their team. There's several dimensions to this.
Firstly, noticing what they're up to. When there's notable things they achieve, a high performing CDO will point that out. They will always aim to say that to them personally, one to one. But often it's also important to do that in a public forum, to note what they've done or contributed and thank that person so that peers and colleagues see that public praise as well — in a shared communication space, like a chat channel, internal newsletter or group email, say.
Ideally, you'll be doing that for people outside your immediate team(s) as well — there's plenty of places and spaces where larger internal groups are convened, for multifunction initiatives or 'town hall' events, for instance.
And where you can, it's good to do that for your customer and their team members, too. Notice things, and say a personal and a public thanks to them … and make sure that's passed up their management chain too, if you can.
Secondly, the CDO has the back of everyone in their team. When there's difficulties of whatever sort, the CDO is there and able to lend a hand.
That may mean helping directly, or finding others who can. But that also means making sure the burden is shared and no one is struggling or suffering alone.
And thirdly, the effective CDO is looking for the best for their team. That means looking our for opportunities — to try out something new, to participate in an initiative, say, or work alongside someone who can help them take a step up; to get some training, attend a course or class, or present at a conference, maybe.
Cheerleader for initiatives #
A capable CDO is also hunting out problems and then looking for ways to solve them. We'll look at 'problem-sourcing' as a practice or methodology elsewhere, but for now we'll just say that it is just as important if this is a something that comes from someone in the team as anywhere else, just as useful if it's a 'this is an annoying/frustrating thing, grr,' or if it's an 'oooh, this looks like an interesting/novel way to raise our game' thing.
Some may only need small tweaks, but others may require a larger approach. Where that's the case, you'll probably need to dedicate some time, people, and resources to it. And when there's an initiative to respond to a problem, it needs the weight of your position to give it support and to champion its outcomes.
Recruiting good people #
You'll also need to recruit people, good people, to join your team and your company. Running effective appointment processes is key to this.
There's lots to say on this, most of it is stuff that has already been said well elsewhere. What I would say in particular is that 'structured interviews' are especially powerful, and I'm a rather big fan of 'situational structured interviews'. In essence, structured interviews try to make it possible to compare apples with apples by asking the same questions to each candidate. Situational questions try to prevent people gaming the interview — they ask hypothetical and forward-facing questions, often based on a mini scenario, ‘what would you do … ’, etc., so that candidates use their reasoning rather than just rely on their work history (which privileges the experienced).
If that's something you're unfamiliar with, I highly recommend you do some reading to find out about it — this introduction to structured interviews from Indeed is as good a place to start as anywhere, but do please read further than that.
Calm under pressure #
The CDO's duty is to bring order and consistency to complex things, and smooth projects and reliable outcomes are the hallmark of a high performing delivery director.
Inevitably, though, difficulties arise. In these circumstances, the CDO is the beating heart of things and the way you respond under pressure has a fundamental impact on your team, your customers, the projects, and the wider business.
The art of plate spinning #
Normal business will mean multiple client projects, departmental initiatives, whole-business targets, and so on running simultaneously. In particular as CDO, you will have a strategy that you're trying to execute, one that will have numerous strands to it.
As with a circus performer keeping plates upright and spinning in the air, many of these things will progress under their own steam for a while but will inevitably require you to intervene to encourage them to progress as needed — towards the right customer outcomes, in support of organisational goals and priorities and so on.
At times, several plates will begin to wobble at the same time, requiring simultaneous intervention. That can be exhausting.
And at times like this you will need to evaluate just how many things can run in parallel, whether your attention and focus (and that of your team and wider colleagues) is becoming too dilute.
Most importantly, you will need to regularly take your pulse (and that of your team) to guard against being overburdened or worse. Burnout will be catastrophic, for you, your colleagues, and the business.
Nonetheless, a high performing CDO will necessarily be a master at spinning plates. And whilst the ability to give due focus is important, hyperfocus that excludes attention on multiple things simultaneously could be problematic.
Plates of paradox #
There are some paradoxes in keep multiple things running simultaneously.
👉Whilst organisational change is integral to your work, and business transformation is inevitable, continuity in corporate identity is vital for it to be meaningful.
In other words, change must be balanced by stability.
👉A key outcome of your work as CDO is consistency. High quality project delivery and customer outcomes that can be relied on, time after time, are critical to the success of the business. But consistency can harden into rigidity, which may result in stagnation.
Instead, consistency should be seen as a foundation for jazz — for innovation and experimentation, a safety net that enables you and your teams to embrace new technologies and new approaches to achieve better outcomes.
In other words, consistency must be balanced by variability.
Tamer of chaos #
Your delivery strategy will be oriented towards being systematic and bringing consistency to customer outcomes.
In the early days, it's likely that you will have to focus on bringing order out of chaos. Chaotic patterns of behaviour often arise during times of high growth, when practices and methodologies that worked in a smaller business are no longer fit for purpose.
Syde, Europe's largest Wordpress agency, experienced a period of hyper-growth when several large projects in a row meant they more than tripled in size in a year.
Although it was a great period for the business, CEO Alex Frison was aware through it all that they were also not very efficient.
The business was extremely pressured, with no time to share knowledge, to celebrate wins or learn from failures, no time to share tools and practices or to influence the wider business. There were just so few people with time and headspace.
And this was precisely why they needed to recruit a delivery principal.
Beware of chaos addicts! #
Some people are naturally gifted at staying calm when the pressure mounts and the most capable CDOs will likely have this quality.
When there’s arson, the first suspects are the fire fighters.
Karim Marucchi, CEO, Crowd Favorite
Be aware that sometimes this is a mask for a chaos junky — those who are most alive when things get intense.
They see themselves as the calm centre of the maelstrom, the necessary heart of things who makes stuff happen in that upheaval.
These sorts of people are more interested in maintaining an atmosphere of busyness than bringing consistency and calm.
Jake Goldman, president and founder of 10up and partner of Fueled has seen CDOs that perceive themselves as jazz artists — adapting to the needs and expectations of both business and clients. But he believes these are people who thrive in chaos, and that's not what a healthy business needs, especially as it grows into maturity.
Resilience #
The intensity of the CDO's position, the responsibility of delivering big stuff, relentless scrutiny, and the weighty demands of a people-centric and outcome-focused role make for a perfect storm of pressure.
Without effective ways to handle them, these can result in stress, risking poor decision-making, depression, burnout, or other long-term physical and mental health consequences.
Resilience is the antidote to this, something of a necessity for a high performing delivery principal.
Resilience is less about how to manage stress, and more about how you equip yourself with the tools that improve your effectiveness in your role as well as your quality of life overall.
Resilience: nature, nurture, environment #
Resilience is a complex thing, with multiple aspects interacting to determine one's ability to respond to pressure and resist it turning into stress.
Innate personality and character traits provide the primary determinant, but our baseline resilience also adaptable and can be trained, like a muscle — intentional practice can help improve our sustainable performance.
Understand your capacity #
You'll be familiar with 'velocity' as a measure of capacity — it's used a lot in Agile project management to understand how many story points a delivery team can achieve in a given time (a two-week sprint, say).
You could also adapt the concept to understand your personal capacity and use it as a barometer of your risk of overload. In particular, if you're taking on stuff that exceeds your normal velocity then that's a sign that fatigue is approaching if you're not careful.
For example, work that happens outside normal office hours should be a warning of heavey weather ahead!
Manage your cognitive load #
Your brain is your greatest asset but it has a limited capacity. When it's overloaded then everything degrades — so-called cognitive function drops, and fatigue sets in. You can help yourself, though.
- Decision-making is essential, but low-value decisions are a load you don't need.
- Automate whatever you can
- Delegate wherever possible
- Empower by default
- Recognise the signs of fatigue
- Delay big and important things, if necessary
- Be careful how you communicate with a fatigued brain and body
- Never send emails when you're tired!
- Schedule high-impact things for the times of the day when you're most energised
- For some that's the first thing, for others later on, etc.
Rest and recovery is vital, not optional #
Fatigue is so detrimental to your performance that preventing exhaustion must be one of your main aims in life.
Rest and rejuvenation are absolutely essential. Never treat them as an optional extra.
What that down-time looks like is different for each person, but good sleep, good nutrition, exercise, time with friends and family, time in nature, time for hobbies and pastimes — all are things to include, where possible.
Lucky! #
And finally, the successful Chief Delivery Officer will need a healthy sprinkling of luck.
Every CDO will encounter surprising situations, difficult clients, challenging colleagues, a conservative organisational culture, institutional muscle-memory, and any number more things that can make forward progress difficult. Their luck will determine the proportion of each of these they face simultaneously and how much effort is therefore required to overcome the things thrown at them.
Highly competent and capable people can find themselves confronting a once-in-a-century event. Unlucky people might have 3 or 4 in a year. No one can be expected to prevail against such difficulties, let alone thrive.
Let's pray that never happens to you.
But maybe make an offering to the gods of good fortune, just in case.