Discover The Insightful Leader Within

Pitfalls of Seasoned Leaders


Reintroduce Formality to Rise to Executive Levels

Your direct reports may know you are an amazing leader, but are you certain your boss knows? Too often in 360 feedback there is a huge discrepancy between the team’s high ratings of the leader and the lack luster ratings of the boss. With more senior leaders it often stems from allowing the relationship with the boss to become too comfortable and informal. Some of the techniques the leader might have used earlier in their career to ensure they were managing up have been dropped with the false assumption these are no longer needed. Later when the leader is overlooked for promotion, the high potential leader wonders why a less capable leader is promoted.

To ensure your boss knows you not only as a trusted part of the team but also as a great leader, reintroduce the following into your communications:

Give Them Advanced Warning

At some point all managers learn that it’s better to forewarn your boss of any issue that may escalate so that they hear it from you first. However, as leaders become more experienced they tend to forget to do this. Often it is because the leader doesn’t see the issue as that big of a deal; they have dealt with it in the past and are certain they know exactly how to handle it.

The focus however, is not if you know how to handle it, but rather: is your boss aware why it is no big deal and that you know how to handle it? If not, they may be taken off guard when someone escalates the issue to them and not know how to respond. If you think your boss may not know there is no cause for alarm and you have it covered, give your boss a quick call, email or instant message to quickly brief them on the potential issue and your plans to address it.

Think back to how you viewed the issue the very first time you had to address it. If you were concerned, nervous, hyperventilating, scattered – then your boss may be feeling the same way if they hear it for the first time, too. Pick up the phone and give a quick “heads up.”

Elevate Your Measures of Success

Many leaders have set performance measures that are too low-level for executives to really care about. For example if you just trained everyone on a new system and you share that 90% of the 80 employees attending the training rated it as one of the best classes they’ve taken – who cares? Only you do. The executives won’t be impressed unless it aligns to some measure they are held accountable for.

If you can tie your measure to revenue, reducing cost, or reducing risk – BINGO! You’ve nailed it! Instead talk about how the two hour training class provided the necessary skills to use the new system AND that new system eliminates 10 steps and saves each employee 5 hours per week in comparison to the old system; resulting in a total of 450 hours per week saved to enable employees to spend more time on critical strategic issues.

Think in terms of productivity, quality, customer retention, market share, costs, safety, legal action and other measures that matter to both the executive staff and Board of Directors.

Manage Your One-on-Ones

When you meet with your boss for your routine updates avoid falling into the common trap of being overly informal by doing the following:

Have an Agenda. Many seasoned leaders don’t think they need an agenda for their meetings with their boss. Big mistake. Without an agenda, the meeting turns into an informal status update and often veers into discussions of problems and help needed. What do you think the perception is of a leader who is constantly venting or discussing problems and asking for help?

Now let’s contrast that to the leader who has an agenda that is focused on the most important projects and topics and knows exactly what outcomes they need from the time spent together. Make certain that some of that agenda time is spent on strategic issues so the boss can be confident that you are balancing the longer-term business needs proactively as well as addressing the current urgent items.

Share the Successes. Make certain you share your and your team’s successes during the meeting. Talk about how you all overcame a particular difficult problem, how you proactively addressed an issue before it escalated into something nasty or how you are putting the plans in place for a long-term strategic benefit.

Too many leaders are worried that this will be perceived as bragging. This is not bragging – it is keeping your boss informed of important information. It also provides information they can likewise tell their boss and peers about that will build confidence in your team. Thirdly, it demonstrates pride in your team and appreciation of their accomplishments.

Don’t Make it Look Too Easy. Too often seasoned leaders forget to talk about the effort something took or how their prior experience helped solve an issue quickly. Without this information the boss can’t appreciate the value the leader brings. Unless you or someone else tells them, they won’t know how you solved thorny issues by breaking them into manageable chunks.

Don’t be the person who is valued after leaving the company. Sometimes a leader is not appreciated until their absence makes their expertise and capability noticeable to others.

As you reintroduce these approaches into your communication, you will see a marked improvement in your boss’s perception of your leadership and advancement capabilities.