By: Jeff Wissink, Navint Managing Director

Recently I served as Interim Chief Information Officer for a major Education Technology company.  As a lifelong management consultant, this was a new and exciting opportunity for me to “sit on the other side of the table” and come to understand the mindset of the Technology Executive, and how that mindset practically differs from the project-driven mentality of the consultant. The Interim Technology Executive (ITE) has both the objective of pushing the company’s technology agenda forward, as well as the somewhat time-consuming responsibility for the more administrative aspects of departmental leadership such as budgeting, spending and approvals, financial reconciliation, human resources, and team building. Having now had the benefit of some time for reflection, I have compiled a list of things that are worthy of consideration both before and immediately after entering into any ITE arrangement.

First: Align your goals with the overall business strategy (and your boss’ financial goals)

Up front, ask what the company’s 3-5 year strategic vision is. Then ask your boss if s/he is financially incented to help achieve those goals and how he is incented – the more specifics s/he gives you, the better off you’ll be. For example, knowing that your boss is incented on top-line growth versus bottom-line profitability/EBITDA is an important consideration that you’ll need to be mindful of as you’re setting the agenda for IT.

Yes, this may sound obvious, and yes this is definitely an important step at the outset of accepting any new leadership role either interim or otherwise. But, it is worthy of special consideration concerning the ITE, as you will likely not be there for 3-5 years. Spending some time thinking through initiatives that will need to be put in motion to accomplish those goals during your tenure is a good starting point, and when done, should enable a healthy and lively dialog between you and your boss(es) as to how to set your priorities during your tenure.

Second: Understand your role and what is being asked of you.  Then leverage the heck out of your Interim status to drive change.

The reality is that if the company is in need of an Interim Technology Executive (ITE), you’re there to drive some amount of change.  Conventional wisdom around C-suites suggests that interim CIO’s are often hired to address problems that may have frustrated the organization for years, or to clear away issues that may have become roadblocks to the former CIO’s transformation agenda.

So, with the table already being set for a change take advantage of the opportunity.  But, keep in mind there is a host of factors and considerations that will dictate where you are expected to land on the “keep the lights on until the next guy shows up” Change Agent Continuum.  Some of the factors will be the organization’s capacity for change, along with the personal and public anointing by the CEO of you, as said change agent.

Considerations that you’ll have to balance against the organizational factors might include existing in-flight programs, current IT organizational performance and capabilities, company culture, and “transformation fatigue”.

Driving change is what a well-leveraged ITE should be asked to do, and the ITE has a distinct advantage in this regard.  As an ITE, you are not making a career there, and so in some regards you can do what needs to be done without fear of political repercussions.  Said another way, if there are things that need to be done, whether they are unglamorous infrastructure improvements, organization redesign, killing off projects that don’t support the business strategy or won’t return a positive ROI in an acceptable period – they’re all fair game.

Of course, in this environment you need to be prepared mentally for the challenges and frustrations that come with being a change agent and an interim executive.  It will be critical to your success, and your career, to stay in constant communication with your sponsoring executives and the CEO.  So have a well-documented set of responsibilities and have frequent meetings- – every two to three weeks, with the CEO or sponsoring executive to assess progress, identify roadblocks and get candid and direct feedback.

Third: Find and fix a few “Quick Wins”

As an Interim Technology Executive (ITE), by design, you are not expected to be in your role for a long time.  With that, it is important to find a fair balance between achieving enough individual success such that you’re credible and Setting the Table for your successor – a topic I’ll discuss in a future post.

When you first step into the position, you will quickly identify the “hard stuff.”  While not necessarily the big, complex and complicated projects, they are the initiatives that might have challenges, or perhaps projects that might be “politically hard” to achieve.  They are projects fraught with some entanglement, possibly ones that were unpopular decisions or things that the predecessor did not want to try and tackle.

Focus your time and attention on understanding these projects – the scope, resources, timing, budget but most importantly the value that you’ll deliver to the organization if and when you decide to resuscitate them.  While you’re getting under the hood of these hairier initiatives, there will be that one project or irritant to the organization that, with some amount of paying attention to it, you will be able to execute on and solve.  Ideally, this is some kind of user-facing inefficiency that touches many people in the company – think underperforming desktop support or maybe a help desk.  Identify it, put some elbow grease into it, solve it, and celebrate it.  Delivering a large, and public, quick win will reinforce your ability to execute and deliver value quickly.

If you’re lucky, you’ll identify several things you could do that fit into the “quick win” category.  Do just enough of them to build the credibility and “bank the points” you’ll need to spend later on fixing the hairy stuff.  Keep in mind, you’ll want to try to leave some projects- both easy wins and interesting ones for your replacement.

Fourth: Setting the Table

As I mentioned in my last post, one inarguable fact about the role of the Interim Technology Executive (ITE) is that the role is interim, and as such it is important to find a fair balance between achieving enough individual success such that you’re credible and Setting the Table for your successor.

Setting the table means setting up your successor for success, and it takes different forms.  Inevitably it means wielding your ITE sword (recall post #2: Leverage the heck out of your Interim status to drive change?) and making the hard decisions so that your successor doesn’t have to.  Decisions like the politically unpopular (but necessary) reorganization of the department, killing non-value added projects, or a host of other potentially unpleasant things that your successor would like not to have to deal with when they get there. Trust me, they’ll thank you.

Alternatively, you might want to nurture a few in-process projects that you can hand to the successor and allow them to claim the victory.  Or, maybe you’ll be able to set the table for a project that can start right away, with most of the foundational work- budgeting, phasing, resource alignment, and stakeholder sponsorship, all done.  Your successor just needs to push the “go” button.

Lastly, Setting The Table means setting realistic goals and timelines for the projects you are committing to and especially to the extent you are taking on longer duration projects that are likely to outlast your tenure.  Don’t over-scope and overset expectations so that the new executive has to bring immediately forward bad news. With the skids sufficiently greased, your successor will have a much easier time making meaningful progress when they arrive, and also diminishes the chance that the company calls you back in three months and asks you to come back.

Fifth: Understanding and Using Sources of Power

As an Interim Technology Executive (ITE) your success will come in part from building bridges with people who will help you accomplish your goals.

Power is the ability to get things done, sometimes over the resistance of others, sometimes with the full support of others.  There is plenty of research on power and this post isn’t intended to bring new thinking forward on the topic.  One common perspective, however, is to recognize that there are formal and informal sources of power inside any organization.

To be successful as an ITE, you’ll need to learn how to use both formal and informal power structures to influence the behaviors of others in the organization.  For example, the formal power for decision-making around departmental or project funding resides with the CFO, but informal power structures may also exist in the Finance Department that is even more important to align with regarding achieving the desired outcome.  Are project funding analysis and recommendations relegated to FP&A, for example?

Outside the CFO office, it is also important to create and leverage a strong business sponsor.  For example, putting in a new sales platform that will improve sales effectiveness and drive incremental revenue will obviously require strong support from the senior sales executive.  Truly collaborating with this individual early on not only develops that elusive “bridge building” between the business and IT, sets delivery expectations, roles and responsibilities and the like – but also builds a strong ally in helping you get the funding you need to achieve the strategic goal.

To be fair, Understanding Sources of Power isn’t something that is specific to the ITE, but for those charged with change, it’s something you must work to understand.  Given your role and tenure, as an ITE, you just need to do it more quickly.


Sixth: Take Accountability

How many times have you worked at a company where “the business“ and IT had a relationship where IT was viewed as a strategic thought-partner with a critical seat at the table in helping the business achieve its goals? It shouldn’t take you long to answer that.

The sad reality is that distrust, cynicism, and sometimes even downright open hostility between business functions and IT is more common than not. It is often the reason you are there to begin with. IT is typically underwater, with way more projects and demands from the business than budget and people to accomplish everything, and why does the business keep changing its mind about what it wants anyway? From a business perspective, IT is too slow and wants way too much money and involvement from the business to get the simplest of activities completed. Why is this so hard? My husband/wife/partner/cousin/dog works for a company and they implemented XYZ solution in 4 weeks!

Stop me if you’ve heard this before.

Kidding aside, conflict between these groups is as old as the groups themselves. And while addressing and even fixing this conflict is an admirable and even achievable goal over time, you as an Interim Technology Executive (ITE) will likely not be able to solve that during your tenure, my fourth blog post on “Setting the Table“ notwithstanding.

However, what you can do is start to break down those political barriers by taking accountability for the performance of your group. There is a shocking lack of performance accountability in corporate America, as corporate behavior tends to punish even calculated risk-taking and certainly failure. Given this behavior, it is often a lot easier to try and pass the blame along down the line than own up to your portion of the blame when screw-ups inevitably happen.

In those environments, it is incredibly refreshing when someone stands up and says, “Yep, that was our bad. We didn’t execute that the way we should have. Here’s what happened, and here’s how we’ll do it better next time.“ As an ITE, you can do this without fear of repercussion, and be the breath of fresh air that not only starts to break down historical mistrust but also provides credibility and even a platform to make larger, more systemic changes if needed. As walls start to fall, the business might even own up to some things that they could do better in the future.

I’m not saying you should fall on the sword unnecessarily; far from it. But if we’re honest, some of the ill-will that exists between IT and the rest of the business falls on you and your team, and some of it doesn’t. Owning the occasional underperformance of your team is a luxury that will empower your ability to Use Sources of Power and get things done.


Seventh: Go Native

On the last day of my most recent interim CIO experience, my boss (the CFO) threw a small going away party for me, inviting my full staff and the management team for one final fare-thee-well happy hour. During the event, he gave a quick speech, and thanked me for my contribution to the company over what had been a significantly longer period of time than was initially projected. He also said that one of the things he was most thankful for was the fact that I “never acted like an interim guy,“ and how that was important in terms of rapidly gaining the credibility with the business to get stuff done. But you’ve heard me talk about the importance of quickly building credibility before.

While it would have been easy for me to not take the fiduciary responsibility of budgets, long-term financial planning, and spending as seriously, or to de-prioritize the care and feeding of my staff – the fact that I did take those things seriously and went “native“ – acting like this was my fulltime job, was a difference-maker. While I didn’t necessarily realize that I was doing it at the time, I’m particularly proud of that observation. And if I’m being honest, a lot of those things that I took seriously were fun. Maybe it’s the result of many, many years on the other side of the negotiating table, but haggling with vendors for price concessions was fun. Negotiating with other internal funding sources as to who would pay for what as it related to current and future project work was fun. And providing candid feedback and professional development advice to my staff as the guy that’s been around the block a few times was also fun.

Going native makes people comfortable. It makes people not question your motivations. You’re there to work in the best interest of the company that’s brought you on, even if the best interest of the company outlives, by design, your interim status.


Eighth: Define and Find your Ideal Replacement

At this point, you have leveraged your Interim status to drive all kinds of positive change. You’ve fixed broken processes, designed and implemented the perfect customer-facing organization, finished off a troubled project, set the table for your successor, and undoubtedly learned a thing or two. Hopefully you’ve imparted some of that battle-earned wisdom on others as well. The group is stable, and you’re ready to pass the baton. It’s time to go.

No one knows better than you the kind of person it will take to succeed as your successor. Make sure you’re plugged into the recruiting process from the very beginning, and that you’re working with Human Resources/Recruiting to define and document the key characteristics of the ideal candidate.

Once you have a loose alignment on the key characteristics of that candidate, you can start to talk about optimal recruitment methods and costs involved to attract that person to come to work. Any reasonable recruiter will have (or be able to get) location-specific salary benchmarks for the jointly-defined position. In some cases, the business will have the appetite to pay what’s required, but in some cases they won’t. This is a critical alignment point, and skipping over it will only waste time and cause frustration. Either work to get the company comfortable with paying what’s required to get the right person, or reset expectations on the kind of person they’ll be able to attract – and articulate the associated risks.

Also, make sure you understand and express all of the components other than compensation that will make the role attractive. For example, if the company has a strong social mission, you will likely find recruiting success by marketing both the cause and the comp. Culture, job structure, and people can all be differentiators – use the best of all of factors to market the opportunity.

Lastly, consider the timing. There is a natural “right time” for you to leave, and not properly considering the natural recruitment lifecycle will likely find you in the position longer than you intended, or worse yet, find the company rush to a less-than-ideal replacement. Basic right-to-left planning based on all of the factors above will dictate how early in your tenure you need to start the planning and shepherding process. It’s not always easy to get the timing to align perfectly, but leaving a well-organized group in the hands of the right person at the right time is a critical component of your overall success.


Ninth: Communicate. Communicate. Communicate.

Communication is one of the most important things that you will need to do as an Interim Executive. Or perhaps more appropriately, fixing communication is one of the most important things that you will need to do as an Interim Executive.

Few people would dispute the fact that communication with management, your peers, and your staff is a critical activity, for all of the obvious reasons. And yet given this broad consensus, it’s surprising how few people apply any kind of methodical approach to departmental communications. What results is a somewhat haphazard and inconsistent set of communications that emerge from your group – with some people feeling like they are getting more information than they need (and summarily begin to ignore you), others feeling like they’re not getting enough (and begin to make noise about not knowing what’s going on), or even worse yet, people getting the wrong or wrong level of information. All of these eventualities are bad, and lead to unnecessary misunderstanding, distractions, and if left unchecked for too long, even ill-will.

The good news is that there’s a fix for this, although it does require some initial thought, planning and periodic revisiting. I use a simple tool called a Stakeholder Analysis.

  • Create a stakeholder list. Define, either by name or department, a list of people who are affected by your department’s actions. Make sure you’re including not only executives, but also peers, staff, and others in the organization. As an Interim Executive, chances are that this list includes everyone in the company. Be methodical about listing those people and groups, and make note of individual/group role, and physical location/timezone – so you avoid scheduling live communication events in the middle of the night for your office in Hong Kong.
  • Assign individuals and groups into something called “Audience Groups.” People and groups are assigned to Audience Groups as they desire the same level of communications in terms of content, cadence, and method. For example, you may decide to group all CEO Staff into a CEO Staff Audience Group, as they might simply be interested in a monthly (cadence) project update (content) delivered by e-mail (method.) Should you be so lucky.
  • Develop a communication plan for those Audience groups. An “Everyone Else” Audience Group may simply be recipients of a quarterly newsletter or access to a blog. Consider both “push” and “pull” communication methods – one is presented to your Audience Group member (e-mail, in-person meetings, newsletters) and the other the Audience Group member gets as he or she sees fit (intranets, blogs, social feeds, etc.) Use all of the tools at your disposal.
  • Drop all of the communication events into a calendar, so that you know what needs to be developed and delivered to whom and when, and make sure you have someone (or a team) who can keep tabs on the calendar and assist in content generation.
  • Revisit the stakeholder analysis from time to time, and always revisit the tool when a communication gap is found.

There you go, a simple tool so that you’re always on top of your comms. Email me if you’d like to see a simple Excel-based template.

Tenth: Be There

If you’re taking on an Interim Technology Executive opportunity outside the area where you live, be prepared for heavy travel to that location. It’s especially important to be there at the beginning of the duration, on-site with your adoptive company and team, if you are to be successful in the Interim Technology Executive role.

I realize that this might sound a little strange, presumably coming from a technology person. Personal contact in this day and age? Can’t we just text each other like the kids do? While there is no doubt that advances in cheap collaboration software have made it easier to stay in touch remotely, there is simply too much that you miss when you’re dialing in.

If there is a consistent theme amongst the previous nine posts that I’ve submitted on the Interim Executive topic, it is that there are things that you need to do to be an effective agent of change. At its core, an Interim Executive is exactly that, a Change Agent – and if you’ll grant me that, it then follows that your score as an effective Interim Executive should be determined by the effectiveness of your ability to change the organization for the better.

And when was the last time you really changed something for the better over the phone or in an email?

I’m a lifer on American Airlines, and while I’m thankfully still pretty far away from my congratulatory onboard visit from Sam Elliott, and for as much as I don’t enjoy traveling for business like I used to, it’s also become exceedingly obvious that many times important work conversations happen outside of scheduled meeting times – over lunch, ad-hoc meetings and discussions around the proverbial water cooler, and after hours. If you’re not there, you miss those things. From a Change Agent perspective, those things can be as important as your regularly-scheduled meetings, or even more so. Second, technology advancements aside, emails, conference calls, and yes – even video conferences – are incredibly poor communication mechanisms, as everyone who has been on the receiving end of a poorly-worded email and resultant swell of massive, abject confusion and non-productive claptrap can attest. Sorry kids, in 2016 at least, real, rich, synchronous communication can only be achieved in person. Lastly, the fact that you are traveling and presumably making those personal sacrifices to be there is a subtle, yet understood, show of your commitment to the job to those around you – your bosses, your peers, and your team.

It’s important to consider this before you accept the role. If you can’t afford the time “Up in the Air,” then you’re probably better served to pass on the opportunity.

Eleventh: Check your Emotions

In my last post, I talked to the fact that at its core, an Interim Executive is a Change Agent – and that your score as an effective Interim Executive should be determined by your ability to change the organization for the better.

In many cases, changing the organization for the better has a dramatically positive impact on many individuals’ lives, as restructuring, streamlining, and optimization activities will open up new opportunities for people in the organization. Knowing the high-performers within your group will allow you to effectively unleash untapped potential in your organization, providing new opportunities for leadership that may not have previously been feasible.

However, changing the organization for the better does not mean that you’re changing everyone’s lives in the organization for the better. In most cases, restructuring activities change departmental responsibilities and individual job descriptions, and may even eliminate the need for functions and people altogether. Said alternatively, restructuring the organization for the good of the company will often come at the expense of certain individuals, and regardless of your experience with such matters, “rationalization” activities are never fun.

So when faced with the human element of the change you’re driving, Check your Emotions. Anticipate that there will be moments of emotional highs and lows as you strive to better the organization, and remain rational, firm, and fair. There will be moments of triumph, and many people will be better off for the fact that you are there, but the truth is, being a successful Change Agent also requires you to have thick skin.

Twelfth (and final): Take care of yourself and your family

Being an Interim Executive is hard. You’ll work very hard, under pressure, with high and sometimes unrealistic expectations placed on you, put in long hours, and be away from home more often than not. With the stress and wear-and-tear of the job, it is easy to inadvertently de-prioritize other things in your life, falling into bad health habits, for example, or maybe missing a few too many Squirt hockey games. Unfortunately, this can have a spiraling effect, since bad consumption and sleeping habits during the week inevitably roll into the weekend when you are home with your family, and you’re more interested in catching up on sleep and relaxing than necessarily spending quality time with friends and family.

In HR-speak, this is what would be called a “development opportunity” for me personally. My wife Lisa is nothing short of a saint for putting up with me and picking up even more of the slack during these periods of high activity and stress. It’s one of the things that I’ll focus on doing differently next time.

So take it personally, yes. Take accountability, yes. Change people’s lives for the better. Throw yourself in and leave your host company better than where you found it. Do all of that while keeping it in perspective of your life goals. And once you figure out how to balance all that, please let me know.

Thank you to everyone that has taken the time to read this. Writing it has been cathartic for me, and I have received some great feedback, fair critique, and encouragement to continue from many of you. Always feel free to drop me an email to continue the conversation, I can be reached at


About Our Blogger: Jeff Wissink is a Managing Director at Navint Partners, LLC and over his 20-year consulting career he has led Enterprise Transformation, Process Improvement, and IT Strategy projects across a number of industry verticals including Media, Consumer Products, Apparel & Retail.

Jeff also offers special thanks to Michelle Garvey, CIO at J. Crew for seeding many of these practical tips with him as he started on this journey.