Guidance to IT Leaders: Preventing Surprises

No one likes surprises at work. Most people don’t even like to be surprised by donuts in the break room. (“Aw, shoot! If I’d known, I wouldn’t have grabbed a breakfast sandwich on the way into the office!”) The only acceptable surprise I ever want to hear about at work is better-than-forecasted financial performance. One of the most important responsibilities of any leader, which you will never see listed on a job description, is to prevent surprises for your leadership.

You can’t prevent unexpected things from happening, especially in information technology. But, you can help lessen the shock and anxiety they cause your executives and business leaders, primarily by managing expectations.

Here is a great example of managing expectations:

John was away on a business trip. He called home to check in and ask how everything was going. John’s son replied, “Everything is fine, except the cat died.” John was distraught at the loss of his beloved cat and took the opportunity to coach his son on tact. John counseled, "In the future, when delivering bad news, try to be more diplomatic and soften the blow.” His son asked “How should I do that?” John explained, “Well, you could tell me that the cat had climbed out onto the roof. And then you could tell me that the cat was injured. Next you could explain that the cat was being treated at the vet. And finally, you could tell me that the cat had died." His son seemed to understand.

The next day, John calls and his son answers the phone. After a short conversation, John asks how his mother is doing. John’s son replies, “Well, Grandma’s on the roof.”

<sad trombone>

In all seriousness, you can lessen the impact of unexpected events for your boss with your communication style at each step of the process. As we walk through the stages, consider the various kinds of surprises you might be faced with: unplanned system outages, information security breaches, personnel issues (major policy violations, resignations, accidents/injury), etc.

Before the Incident

The best way to prevent surprises is to ensure your leaders are aware of risks and understand that unexpected incidents can and will happen. From an information security perspective, you should be conducting regular risk assessments and then summarizing and communicating the results and recommendations. On the infrastructure side, capacity monitoring and issue management are effective tools to forecast future investment needs. Developing a sound IT disaster recovery plan is also a great opportunity to remind your boss that “stuff happens” and when it does, here’s how we’ll deal with it. Those proactive conversations about what could go wrong will help alleviate the emotional impact of surprises later. 

Immediately When an Incident Occurs

Don’t wait until you have all the information about an event to update your leadership. You might not even know exactly what happened yet, but you should let your boss know that something is going on. Next, you need to instill confidence that you are doing everything you can to resolve it. Reassure them that you will do a full investigation to determine the root cause and preventive actions. Finally, commit to providing regular updates. Your first communication might say something like this… “I wanted to let you know that <critical technology service> is currently down. I don’t have a clear answer yet as to what happened, but my team is working on it right now and I am engaging all the appropriate parties to restore the service. Once we have it up and running again, we’ll do a full analysis to determine what happened, why it happened, and what we’re going to do to prevent it from ever happening again. I’ll update you as soon as I have more information, or in an hour if I don’t.”

Throughout the Incident

Frequent updates, even if you have no news, will put your executives’ minds at ease, knowing that you and your team are still focused on the issue. Every update should reiterate your commitment to resolving the situation and then identifying the cause and corrective / preventive action. Do not use these status updates to begin speculating about who is to blame, pointing fingers at vendors, or getting defensive about the cause. Keep your communication strictly limited to information relevant to the resolution. Even if your boss wants to know who is responsible, try to explain that you can’t divert resources to that kind of analysis until the problem is solved.

Unexpected events will happen, but you can use them as an opportunity to demonstrate your level-headedness and ability to remain focused in the face of challenges—a huge component of executive presence. But those aren’t the only kinds of surprises you need to protect your boss from. 

Escalations are unwelcome surprises and damaging to your reputation. It is so frustrating when one of your customers is dissatisfied with their technology services and chooses to go over your head and escalate the issue to your boss. The culture of the organization will determine if that behavior runs rampant, or if it is discouraged. But, how can you attempt to prevent, or at least lessen the impact of escalations?

First, identify the people who are most likely to escalate their complaints to your boss. You probably know who they are, because they are the ones who already have done so. Or, they frequently escalate issues over the heads of your employees by coming to you. You should also identify the key stakeholders who, even if they don’t escalate issues to your boss, it would be very damaging if they did. That list would include your boss’ boss, the owners of the company, and other influential executives higher than you on the org chart. Finally, make sure you include the unofficial power brokers at the company: the office manager, the head of HR, executive assistants, and the owner’s kid.

What do you do with that list of people? Check in with them regularly to find out if they have any issues or concerns. Pick a day and time—I like Friday afternoons for this task—to walk around or make phone calls to these folks. Proactively inquire how their technology systems are working. Ask probing follow-up questions. Follow up on any issues immediately. Keep these people happy so they have no reason to escalate above your head.

But what if they do have issues that your team is struggling to resolve? Will you even be aware when that happens? If there are several levels of separation between you and the help desk, you may need to implement a formal process to keep you informed when key constituents are experiencing ongoing technology issues. But, even in a small company, you may not be aware of their problems. You could simply ask your team members to let you know if certain internal customers have open tickets that haven’t been resolved right away, or repeat tickets about the same issue.

What do you do with that information once you have it? If you can help with resolutions, great. But, that’s probably not likely. You can make an extra PR visit to those individuals experiencing problems to let them know you are aware of their issues and that your team is working on it. But, that only goes so far. Once you are aware that one of your high profile customers is having problems, you should casually mention it to your boss. Your update should sound something like this, “This is not a big deal, but I wanted to make you aware just in case you hear about it from someone else. Janet is having intermittent problems with her remote access again. My team has tried to replicate the issue but haven’t been able to do so yet, which is making troubleshooting difficult. We’ve pulled in additional experts to look at it, but I can tell Janet is starting to get frustrated. I normally wouldn’t bother you with a help desk issue like this, but I didn’t want you to be caught by surprise if Janet mentions it to you. Be assured that we are doing everything we can and won’t stop until we figure this out.”

With that comment, you’ve gone a long way in protecting yourself and your team from potential damage to your image. Now, if Janet does escalate to your leader, they won’t be caught off guard. Instead, he or she can appear informed and competent, and will be much better equipped to support you. Hopefully they will be able to tell Janet, “Yes, I heard about your problems, and I’m sorry that’s happening. I know the IT team is working hard to figure it out.”