Your first 30 days in post as CDO

It's best to approach this from two directions. First, what are the questions that should be on your mind in those first 30 days? And second, what practical things do you want to achieve before the first month is out?

In other words, what are you trying to understand initially? And how can you actually do that?

Let's dive in.

The Questions on the CDO's Mind #

Although there'll be lots of questions you'll want to ask at the beginning, there's some specific things that should shape how you start trying to gauge the state of play.

What’s going on? #

Starting in a new role as Chief Delivery Officer, you're walking into an organisation that’s accustomed to a certain way of working. We've just looked at the challenges of interpreting and evaluating business-as-usual, so there's no need to reiterate here. At this point, rather than getting your hands around ongoing customer projects, the day-to-day of product development, or other aspects of BAU, instead you're mind is on how the delivery unit and individual teams are operating.

Taking the temperature #

Although the interview process before you start should've laid out the most important issues to address there's only so much you can find out in that context, and there's a strong chance that some aspects may've been actively hidden from you behind a veneer of sorts.

In this first 30 days, fully understanding what you're letting yourself in for is fundamental.

To do that, you need to use your thermometer to take the temperature of the organisation. You're trying to find out not so much what the business does but how it does it.

And that starts with listening. Lots of listening. Going out of your way to listen. And then listening some more.

Take as much time as you can to meet with people. Invite people for morning coffee, or lunch, or afternoon tea, or a walk around the block. Travel to where they are, if they're in a different office and you can — making an effort and meeting in person is powerful. Meet on a video call. Whatever. Just meet with people.

Ask open questions, about the challenges they're facing, the opportunities they see or needs they have, give people lots of space to talk about their priorities.

• What are they concerned about?
• What keeps them awake at night?
• What are they really proud of?
• What chances do they think the business is missing?
• Where do they see friction in the way things are done?

You'll be amazed to hear how some delivery difficulties are actually interconnected company-wide issues.

Who should you meet with? #

In the main, it probably means department heads or leaders of teams or units within the business, but don't overlook talking to regular team members as well. You should be trying to look at things from as many different angles as you can to get a full and complete picture.

Everyone is busy, but directors and execs are notoriously hard to get time with. That said, they'll probably have a shopping list of things they need help with, probably a bunch of things that you can offer to get involved with for them, and that may be your way in.

And make sure you go beyond your part of the business, too — colleagues in product, sales and marketing, customer support and client success, legal, finance, operations, and so on, all have important perspectives on things that you'll be feeling from the customer delivery end of things.

What to listen for #

As you talk with folks inevitably they'll tell you about problems, and you should be particularly attentive to the things that are being brought to the surface. Some will be obvious, others less so and may only be apparent when you've had some time to reflect.

You can use these questions as a personal prompt as you let all these things marinate in your mind:

• What are the problems, as you see them?
  • Where are these issues in the business or delivery cycle?
  • Do you need to ask some follow-up questions to verify or clarify things?
• Are they aware that they have problems?
• Are they aware those problems need tackling?
• Do they understand the problems they have?

As you're listening, be aware particularly of responses like:

• 'oh, that's the way we do things around here,' or
• 'well, that's how Serena/Jeff/whoever prefers things to be done,' or worse
• 'ah, we've tried that before and it just doesn't work for us'.

They may suggest other deeper seated problems to pick up.

Who's got their hands on the reigns? #

Every organisation has its internal politics, the tensions over status, power, the direction of travel, and what's considered 'best' inside the business. You may not want to be involved, you may not need to get involved, but you'll definitely need to understand the political dimension of the organisation.

A full understanding may be a tall order for the first 30 days but you'll need to do your best to examine it, specifically so you can avoid treading on trapdoors or, worse, landmines through unwitting missteps.

There are people whose support you will need or whose agenda you will need to align with, key stakeholders or sponsors, as you seek to make changes in the business.

There's a more pointed aspect of the politics for you, though.

Who's making delivery decisions? #

The more direct impact on your area of the business is who's actually making decisions about project delivery.

As you're eating your body weight in cake and listening as people talk, you'll be wanting to understand what determines how customer outcomes are achieved.

You may find there's disconnected commitments made by the commercial division. You may find overreach or excessive caution in the legal department. You may find HR processes that put unhelpful brakes on hiring. You may find executives or other senior leaders who are irrepressible micromanagers. You may find a CTO or principal engineers who have a single hammer in their toolkit, and everything looks like a nail. Or any number of other issues.

Whatever's going on, you need to get to the bottom of the factors that shape delivery decisions.

• How are customer delivery decisions being made?
• How do they get made that way?
• What’s driving them?
• And why?

The answers you find to these questions are a vital component in your assessment of the state-of-play during this first crucial month.

Finding the room where it happens #

While you're talking to all the stakeholders and interested parties in this first month you should be on the hunt for the heartbeat of the organisation. That may not be the executive team or board meetings, necessarily — it may be going on elsewhere.

What are the crucial meetings or events where things get decided or actions chosen? What do you need to get invited to? Who do you need to be connected with in order to be properly 'plugged in' to the business? Are there particular people or events that act as gatekeepers or conduits to progress? And can you help out?

How did we get here? #

Part of understanding the politics, the patterns, and the problems of the new organisation is understanding what's happened to bring the business to this point, hiring you. Or, to phrase it differently, you want to understand the history you're walking into.

That's a tall order for your first month, but you probably ought to make a solid start on unpacking the backstory, even if that's just the most recent stuff.

We've already discussed joining in the middle of business-as-usual, where we covered the headlines of the areas to assess to gauge the story so far. There's no need to rehash that here.

Rather, your focus in the first 30 days is on getting a headline view of the lie of the land.

Of the subjects highlighted before (practices; tooling and systems; governance; planning; processes; organisational structure; metrics, analytics, learning; supplier relationships; team dynamics), your conversations should give you a sense fairly quickly of the areas that may be causing problems. Once you have a sense of the areas of concern, you can then conduct more of an in-depth exploration in which you'll look at the decisions and the events that resulted in the current situation.

Quick wins, and their perils #

In the first 30 days, new CDOs often want to prove their worth or value to the business. Often that means keeping an ear out for one or two obvious things that are causing friction, easy things to pick out and change — the quick wins, the low-hanging fruit. You may even have people coming to you with suggestions of things to do that, with apparently small effort, would make a big impact.

Consider these carefully.

At this point in time, you have the least amount of knowledge of the business and its ways of working. That means there's a lot of stuff you don't know, especially the ramifications or consequences of any changes you may make.

Ask yourself some questions:

• If it's such a good idea, why hasn't it been done before?
• If it's so quick to do, why has no one done it already?
• If the benefit is obvious, why are things still messy?

Whatever this is, it may in truth be a Trojan Horse — attractive on the outside, but hiding serious dangers on the inside.

And to say it again — at this point, you know the least about the business. So, be careful of hidden consequences.

If it's a genuine win, if you know for sure there are no problematic downsides … go for your life.

In all other circumstances, though, caution may be the better part of valour, as they say.