Assessing the Technology team as part of an IT Due Diligence or IT Assessment

I get asked this question a lot so I thought that I would share my thoughts on this emotive topic. I keep in mind throughout the process that the question that I am trying to answer here is: "Would I be comfortable investing my own money with this team?". This is not an easy area to cover for many reasons but primarily because you do not see the team in a work situation, you often only meet them for a short time (after all, your role is not to soak up all of their time unnecessarily) and of course, you will most likely only meet the most senior team members.

5/20/20247 min read

To be clear, whilst this is a critical aspect of IT Due Diligence, it is only part of the process. In fact, there is another post in this blog covering my IT Due Diligence and IT Assessment template, which lists all of the topics that I like to cover as I carry out the assessment. There are a number of attributes that I look for when reviewing the technology team, but the most important, by some distance, is the first one of the list below.

Honesty and Integrity

You have to be able to trust this team and in particular, its leader, if the investment is likely to stand any chance of success or the organisation is going to see IT and Technology as a trusted partner and enabler. Why are honesty and integrity so important? To start with, the openness that comes with these attributes is what allows for honest and frank discussions when something is not working out that the organisation wants or planned for. Having those discussions early increases significantly the chances of a successful intervention and let me be clear, things are always going to go not according to plan. This all leads directly back to the capability of the team to deliver what they promised, when they promised it, and that is ultimately what will be a significant difference to the organisation's chances of success.

For clarity, this is not about liking (or not liking) an individual ... it is about irrespective of differences of opinion, do you trust this individual and team to do the right thing. This can be hard to assess based on limited interaction. Sometimes all you have to work off is a couple of telephone calls, where you cannot see the body language. This is particularly the case if the business is at an early stage or the sum of money involved is small. Naturally, I prefer to spend time face to face in order to really understand the leader and the team, as you can pick up a lot of information by just being in the same offices. However, depending on the sensitivity of the transaction or the IT Assessment, that may not be an option. Nonetheless, no matter how the interaction is carried out, it is usually pretty clear if something is amiss, even if you are not sure what it is at that point.

Drive & Determination

Particularly in startups and early high growth technology businesses, the technology team (which can often be just one person, such as a co-founder) has a lot to contend with. Building a product and supporting it, thinking about the future at the same time as mitigating technical debt, can be a very tough role. So I look for personal resilience, grit and a desire to win as I know that these qualities are key to success. This area can be a challenge, particularly around the personal resilience, as there can be an aspect of personal burn-out involved, so it can be important to (sympathetically) ask about this subject. For lone technologists, it is important to be gentle for a couple of reasons; firstly, they will almost certainly be a single point of failure for the organisation and therefore a significant risk and secondly, nobody can be expected to know everything about everything. As a result, I absolutely ensure that none of my questions or comments could in any way be viewed as judgement. It is simply not fair to do so as the individual will be under huge pressure already, without needing me to make them feel any worse. In fact, it is not unusual for us to meet post the transaction and to work together on specific challenges that I identify during the IT Due Diligence. This has a few benefits, namely: a friendly face to talk to who already understands the technology & application and therefore slightly reducing the single point of failure risk, someone to bounce ideas and thoughts off of and of course, someone who can actually take some of the workload off of the individual in question.

In larger teams, the scenario is different as there is less likely to be single points of failure at this level. However, the drive and determination to succeed is just as important. Technology seems to find new and unexpected ways of breaking or misbehaving all of the time and it is important to understand that is in no way a reflection of the team(s) building or operating the technology. What is a reflection is how those situations are managed. For example, if a system breaks then is a temporary "fudge" could be enacted in radio silence and the system just magically comes to life again. Or the same system breakdown could be communicated to the user base whilst the same temporary "fudge" is put in place. The user base are kept up to date throughout with progress and once in place, a permanent fix is designed and with the approval of the user base, put in place. Finally, some sort of monitoring or telemetry is put in place to identify and flag if the issue ever occurs again. As you can see, both paths are valid and solved the system failure but in the long run, only the latter will keep the loyalty of the users and deliver better long term system availability.

Creativity & Planning

I appreciate that these two areas do not commonly get put together, but in this situation I think that they are two sides of the same coin. Of course, I expect there to be a technology plan and yes, I will be assessing how realistic it is. However, I am equally interested in the team reaction to what happens when the "wheels fall off". How creative is the team and how quickly can they come up with an updated plan? In particular, I would want to know if they have already thought about the aspects of greatest risk to the current plan and what they would do if they were to materialise. Of less importance, but still of interest, is gauging just how creative the team can be whilst under intense pressure.

Let's start with the planning. For me, I expect to see at least two levels of planning for initiatives. Firstly, the detailed plans per project or initiative that cover activities and resources and show the critical path through to final delivery. Secondly, a roll up of the detailed plans together with any other non project activities, into a portfolio plan. This plan should show any potential bottlenecks across aspects such as resources, 3rd party deliverables, environments, infrastructure/cloud builds etc. Based on it, I tend to ask for the detailed plans for the potential bottlenecks e.g. the environments schedule, the resource plans per team or the work package/contract with the 3rd party. The existence of these plans is a great start but I also want to know if they are regularly updated and what happens if a deadline is missed. Based on those answers, I can start to understand the creativity of the team.

Creativity is a tricky aspect to assess as it can be hard to see in practise. In fact, the only way that I can get a view is by asking "what if" questions (such as the planning questions above) and listening closely to the responses. If there are pauses during the response then I know that the scenario has not be encountered or considered before and therefore, I am getting a view of creativity in action. At this point it is worth sounding a word of warning. An IT Due Diligence or IT Assessment activity does not in any way reflect "real life" for a technology team and comes with an overhead of pressure to perform that is not found in everyday situations. Nonetheless, my experience is that creative teams tend to do well in this situation and I have noted over the years, a correlation between team creativity, the speed to find a solution to the problem and the diversity of the team. Please note that when I talk about diversity here, I am commenting on how different backgrounds, experiences and ways of thinking enable teams to come to creative solutions to problems rapidly.


I look for a number of aspects in the leader or leadership team, such as confidence, capability to work under pressure and a good IQ/EQ mix. Personally, I like leaders who care about the well being of their staff, as I believe that makes the staff more likely to follow that leader. I also like to understand their experience, their track record and particularly, gain an insight into what shaped them as individuals. Finally, depending on the situation, I look for a capability to sell and customer empathy.

There is no doubt in my mind, that the type of leadership heavily influences the culture of the organisation and that culture is a key component in all of the above aspects. It is extremely difficult to quantify what the culture is like or it's impact, unless you are in the office and even then, you need to be out on the floor and not in an office. I have only been permitted to sit amongst the teams on a handful of occasions (all of them were IT Assessments) and the mere fact that I was allowed to do so, spoke volumes for the culture.

For a more formal assessment, I have seen Belbin used as well as alternatives such as Honey with varying degrees of success.

You may wonder why I did not make leadership my number one attribute as, after all, it is all about the team. That is true and in startups/early stage high growth businesses, all of the above are most likely apply to an individual. However, as the business and their technology teams get larger, the risk from rogue employees/contractors/partners dramatically increases. I have seen organisations laid low by the actions of an individual who was not the leader.

So, going back to my initial question ... would I invest my own money with this team? A lot of the above helps me collect my thoughts whilst I also listen to my gut. Having met so many people over the years, after a while you just get to know if something is right or wrong. Just to re-iterate, this is not about liking (or not liking) someone ... those thoughts have no place in this process. It is about the ability to deliver a successful outcome for the investment or the requestors of the IT Assessment.

If any of the above thoughts resonate or indeed, if you disagree, then please reach out to me using either the contact tab on the right or the details at the bottom of the page.

All the best.