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Having awkward and difficult conversations is part of the job for any IT leader. Fortunately, Dave Patzwald and Mike Wind have expert guidance to help you meet such challenging moments.

Every CIO will face challenging situations during their careers, which will lead to some difficult conversations. By “difficult,” we mean a conversation that is dreaded, confrontational or just plain awkward. If you are not prepared for these conversations, your instincts might tempt you into the wrong behavior.

Here, we describe five specific situations which create those conversations, identify the “tempted” response, suggest a better response, and offer a way to prevent this conversation entirely in the future.

NOTE: While these five conversations are difficult, they are not the only ones a CIO will encounter. At the end of the article, we include some other examples which can be equally challenging. You probably have some that we have missed.

#1. Explain an Unexpected Budget Miss

The Situation

During a staff meeting, a manager shares a large expense item that was not budgeted. You do not have an offset large enough to cover the gap, so you will miss a formal budget commitment. The manager was highly reluctant to share the news and she is now visibly concerned about her own status. You have a history of meeting budget commitments, but now it’s time to prepare the next status report. 

Audience: CFO 

What You Might be Tempted to Do

  • Try to bury or hide the expense and hope that no one sees it.
  • Use techno-speak to gloss over the issue.
  • Punish the offending manager as a lesson to others about the importance of fiscal discipline.

What You Should Do

Proactively notify the CFO and explain the situation. The conversation will be much more difficult if they find it first. Take full responsibility for the miss and do not make excuses or blame your manager. Use business terms, not tech-speak, and do not over-explain. Do not joke about it and do not promise it will never happen again. CFOs are realists and will appreciate the candor and respect given to them. Within your team, encourage early detection to these issues. Punishment will only lead them to hide future misses and create more surprises.

How to Avoid in the Future

  • Create a rigorous, inclusive financial management process which rewards transparency within your team.
  • Support the CFO’s mission by treating them as an ally, not someone to “get things past.” Develop a reputation within Finance for commitment to the budgeting cycle.
  • Meet all deadlines and build a trust bank for those inevitable surprises.

Key Lessons

  • Never hide anything from the CFO (they will find it)
  • Don’t be too clever with your projects and cost centers in an effort to create back-up / emergency funds for the future

     

    Definition of Chief Information Officer

     

#2. Explain a System Outage Without Knowing the Root Cause

The Situation

A critical system goes down which immediately impacts business operations. It’s not a crisis or true emergency, but employees are inconvenienced and frustrated. You do not know what happened, but you are bombarded from every direction - phone calls, email, chat messages and drive-bys. Everyone wants the situation fixed immediately, to know what caused it and a guarantee it won’t happen again - all at the same time.

Audience: EVERYONE

What You Might be Tempted to Do

  • Guess at the root cause and promise an immediate fix.
  • Try to answer every call and email immediately.
  • Ask multiple people to work on the same problem from different angles.
  • Once the issue is solved, make a triumphant announcement and bask in apparent glory.

 What You Should Do

Recognize the issue and re-validate the business impact with your key stakeholder(s). Do not state a guess as to the reason, but pronounce confidence in your team, and provide them cover to solve the issue. Resist the urge to contribute. Once the problem is solved, do not “spike the football” - just share a concise and professional update. Do not provide unnecessary details as to the cause or the fix - other than to say whether the issue is likely to repeat or not. If anyone thanks you, respond only that “this is what we do.”

How to Avoid in the Future

  • Be proactive in your alignment with the business regarding business impact.
  • Coordinate communication - assign a single person to manage non-critical issues through resolution.
  • Include a summary of all issues (actual or near miss) in your regular business reviews.
  • Provide a layered view of IT operations from the simplest level down to the technical details - ask your peers how much they want to know - and adjust the message accordingly.

Key Lessons

  • Always have a common understanding of the business customer impact.
  • Create a formal communications role within the IT team.
  • Develop a method to communicate quickly across the company (when systems are down).
  • Do not assume everyone wants to know how IT works.
  • Do not assume no one wants to know how IT works.

#3. Explain to a Trusted Vendor that You are Making a Change

The Situation

You have a long-term relationship with an important supplier. They have always delivered everything you have asked. The supplier is more than a rep - they have become a friend. You have been through many battles together and you trust each other implicitly. Over time, however, the quality of their services or pricing has become a nagging issue. When compared to alternatives, your trusted supplier is no longer the best option. It is time to make a change.

Audience: VENDOR REP

What You Might be Tempted to Do

  • Find a way for them to keep the business or promise other work in return.
  • Give them the “price” they have to match.
  • After the change, treat the new vendor as an intruder and not give them the same respect as the previous provider.
  • Always compare the new vendor to the old in an unfavorable way.

What You Should Do

Be brutally honest. Tell the first vendor you have an obligation to do what’s best for the company, and despite their personal history, a change is required. Say you would expect the same behavior from them. Perhaps the rep was in an awkward position also - having held back price increases or awarded other incentives which no longer applied - and was under pressure to reset the relationship too.

How to Avoid in the Future

It’s possible to be friends with a vendor, but maintain boundaries. Always be aware of the optics - not only to other executives, but to your own team. Sometimes a close relationship with a trusted vendor can make it hard for your staff to raise legitimate issues on their performance or pricing.

Key Lessons

  • Address business issues separately - do not give a free pass due to a friendship.
  • Acknowledge that both sides have a business obligation bigger than friendship.
  • If the friendship goes away with the business deal, it was not a friendship.

 

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#4. Defend a Current IT Strategy to a New CEO (or new owner)

The Situation

You are midway through a multi-year technology strategy, including applications, business processes and infrastructure. You have a large team of business process owners, implementation consultants and internal IT professionals all working together with a clear mission. However, there is a leadership change at the very top - a new CEO is hired or your company gets acquired. After a little research, you discover that the new leader had a different set of systems in their former role.

Audience: NEW CEO

What You Might be Tempted to Do

Assume the worst. Wait for the inevitable call for a strategy, meanwhile building a DEFENSE, expecting all kinds of challenges to the current approach. Create a very dense PowerPoint presentation with status slides, governance models, and project timelines. Figure out what systems they used in their prior role and have options to switch if asked.

What You Should Do

Go on OFFENSE. Request a meeting to share the strategy as soon as they have some free time. Prepare a simple presentation focusing on the big picture, and demonstrating the broad support for the program across the enterprise. If they want a deeper dive, ask how much detail they would like to see. Ask about their personal experiences with large-scale initiatives and what did and did not work. Do not ask about the software - ask about the business transformation and the impact. Demonstrate full transparency - even some of the stumbles if relevant. A new CEO would treat a “perfect” implementation as a red flag.

How to Avoid in the Future

The best “defense” is a strategy that is based on process and data, not a specific person or technology solution. A strategy that does not have a broad consensus is also vulnerable.

Key Lessons

  • Don’t assume the new CEO’s prior experience with a particular technology was positive (or negative).
  • Never use the technology name as part of the program name (to avoid association).

#5. Recommend Cancellation of a Doomed (and Highly Visible) Project

The Situation

After the excitement of a very public launch, a large program has started to unravel. No single factor is to blame - it is a combination of technology challenges, vendor confusion, subtle resistance to process changes, and overall project fatigue. Concerns are palpable, but not public. While the program is not led by IT, you have gradually become the face of the program since you know the most. Anticipating the project’s demise, business process owners are quietly starting to remove key resources.

Audience: STEERING COMMITTEE

What You Might be Tempted to Do

  • Plow away in silence and wait for a window of opportunity to make the recommendation, such as new leadership or a significant change in business conditions.
  • Start talking less in the steering committee meetings to avoid being blamed for any failure.
  • Work behind the scenes to convince another process owner to make the recommendation to cancel.

What You Should Do

  • First, decide whether the issues are fatal or just resistance to change - often the symptoms are similar. If the program still makes sense, but people are resistant - it might be time to change the people, not the program.
  • What about you? Do you still believe that the program is (a) valid and (b) achievable? If yes to both, then ask for formal commitment from the rest of the team. If not, then raise your concerns openly.
  • Do not base your arguments on emotions - return to the original objectives as the basis for evaluation.

How to Avoid in the Future

  • Set up governance not based purely on tasks, but qualitative assessments.
  • Establish a program charter at the beginning of the program to provide an objective measure of success.

Key Lessons

  • Address warning signs early.
  • Resistance to change is not always justification for cancellation.
  • Do not confuse difficult with impossible.

There are certainly other difficult conversations, which is why diplomacy is such a critical skill for successful CIOs. Here are some others that were considered for this article:

  • Responding to a business leader blaming IT for his group’s problems.
  • Respond to employees about a rumored restructure (which is likely to happen).
  • Explain a cybersecurity strategy to a board.
  • Explain a technology “swing and a miss”.

Healthy relationships can survive (or even thrive) with difficult conversations. Instead of dreading these situations, use the opportunity to build an even stronger mutual trust.

What is a difficult conversation you have been forced to have as an IT leader? How did you handle it, and what did you learn?

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