A checklist article outlining the key areas of focus for anyone taking up a new technology or digital leadership role, this could be as a Chief Technology Officer (CTO) or Chief Digital Officer (CDO).
The first 100 days as a technology or digital leader can make or break you.
You have to learn fast, immerse yourself in the business and go out to speak to your customers, suppliers and partners.
These are the strategies I use when joining a new organisation.
Accelerate your learning
The first task of any successful transition is to learn as much as you can, as fast as you can.
- Study analyst reports on strategy, structure, performance, and people
- Analyse annual reports
- Read articles by employees, customers, suppliers and industry experts
- Talk with your predecessor (if possible)
- Meet your new boss for an informal chat
During the First Week in Role
- Get an office tour to get your bearings
- Familiarise yourself with your work device, calendar, email etc.
- Meet with at least 5 key stakeholders
- Arrange 1-2 hours with your new boss
- Review detailed strategy plans, performance and personnel data
- Meet one-on-one with your direct reports
- Introduce yourself to the team
- Speak to frontline staff and listen to their issues and ideas
- Look through the project, programme and portfolio backlogs
By the End of the First Month
- Meet with more than 20 key stakeholders
- Understand the technical landscape
- Learn about the company’s governance, operating model and procedures
- Find out how suppliers, customers and distributors view the company
- Know your budget and understand the key drivers of cost
Experience the business first hand
- Spend some time out on the shop floor in your branches
- Download your company’s mobile app and browse the website
- Spend a few hours at your call centre and listen to operator calls
- Visit some customers to elicit their opinions of your service
- Check out your competitors
- Visit internal operations to understand the journey your product takes from raw materials, to the customer
- Spend time with your technology teams to understand problems, build trust, and help unblock issues.
Start building a high performing team
Your success will be determined by the quality of your leadership and the quality of the team you build.
Your job is to get the right people into the right roles as soon as you can.
1. Promoting the best internal talent
Giving your top performers the opportunity to step up should be your first area of focus.
This shows that you reward contribution and will create trust within the wider team.
2. Developing and addressing under performers
For under-performers your focus should be on training and mentoring. Those that still fail to meet the standard should be found new roles or exited.
This shows that you are loyal to the team over an individual.
3. Hiring incredible new people
New leaders have the opportunity to bolster their team with great people from industry or through internal moves.
Negotiate success with your boss
The relationship with your boss will be key to your success and you should prioritise time to build this partnership.
There are three important conversations you should have with your boss soon after joining. Your job is to negotiate and agree these expectations so that you both buy into them.
1. Expectations conversation
Align and negotiate expectations around what good looks like.
- What are the key areas that you need to focus on in the short-term?
- What does success look like?
- How will success/ performance be measured?
2. Resource conservation
Understand what resources you have and what you need to be successful.
- Align on the critical resources you need to achieve your objectives
- Discuss gaps and vacancies
- Know the budget required for run and maintain, maintenance and change
- Agree on the current team performance and capability
3. Style conversation
Determine how you can best interact for maximum effectiveness.
- Frequency and format of 121s
- Communication update preferences e.g. email, phone or face to face
- Types of decisions that require sign off and consultation
- Appetite for risk, disruption and change
Find quick wins with “Goldilocks projects”
Quick wins are crucial to building your credibility. They create the perception that something great is happening under your leadership.
Find a couple of ‘Goldilocks projects’ to focus on. These need to be big enough for a significant victory, but not so easy that it can be dismissed.
Some areas to look for quick wins could be:
- Fix technology niggles – e.g. too many passwords, network issues
- Enhance key areas of customer dissatisfaction
- Speed up governance/ change process
- Improve bottlenecks in internal processes
- Areas that matter to your boss
- Projects that align with key business objectives
- Rescue failing programmes
- Expensive or inflexible contracts
- Saving money on a vendor or service
- Key processes that impact customer or operational areas
Create social networks
To succeed you will need the help of many different people across the organisation.
Your job is to figure out how work gets done. This is often very different to the handbook or the documented processes.
Key networks to create are:
- In your team
- In your department
- Department senior leadership team
- Influential people who can help or hinder you
- Technology and digital communities of interest
Understand the technical landscape
It will take a while to deeply understand the technical architecture and technical landscape of your organisation.
Here are some areas to focus on:
- Data centres
- User devices
- Voice, telephony and video
2. Software and application delivery
- Hosting, IaaS and PaaS
- Testing and automation
- Deployment and release management
- Version control/ code repositories
- Delivery methodologies
- Feature prioritisation
3. Operations and support
- Incident Response
- Operational change
- Problem management
- Patching, upgrades etc
- Support/ help desk
- Internal and external monitoring
4. Data and analytics
- Data platforms
- Analytics platforms
- AI/ machine learning
5. Business continuity
- Fail over
6. Commodity software and licences
- Email, calendar, productivity tools
- Central systems – ERP, CMS, CRM etc
- Commercial off the shelf (COTS) software
- SaaS based software
Know your contract, commercial and supplier landscape
Most technology organisations will have numerous, and often complex, IT contracts and licensing agreements.
To begin with, don’t read every contract from cover to cover. Start by focusing on the contract schedules which summarise the key details:
- Cost of the service
- Duration/ term
- Dates (anniversary or end dates)
You may inherit significant contract dispute, contract failure or contracts expiring with little to no opportunity for review. Therefore it’s important to be transparent and building strong relationships with the commercial management team to understand:
- Open or pending contract disputes
- The quality of the supplier relationships
- Contract performance against KPIs and SLAs
- Opportunities for contract extension and/ or run off
Obviously there is no one-size-fits-all when it comes to leadership.
Your job is to start adding value as soon as you can, but don’t cut corners when it comes to spending time with customers, suppliers and partners.
After your first 100 days you should be ready to drive significant business value; cost efficiencies, customer satisfaction, and profit.