The Leadership Challenge: Insecurity – 3 Tips!

The Leadership Challenge_Insecurity 3 Tips

The Point: What do you get when you cross a bully, a know-it-all, an underperformer, a spotlight-grabber, a perpetual reward-seeker, a comparer, an imitator, and tenure? The answer: an Insecure Leader! It got us wondering here at Tip of the Spear HQ just why/how could the trait of insecurity actually take root and grow within a leader in the current workplace. So, in this week’s post we’ll explore the topic of being insecure as a leader along with 3 tips… Enjoy!

So You’re Telling Me You’re an Insecure Leader?

I’m fortunate, in as much, I typically love the consulting work we do at Tip of the Spear (M&A, Sales/Business Development, and Turnaround). However I sometime question my “fortune” when I have an experience that goes sideways, and that’s exactly what happened on a recent consultation visit when insecurity raised its ugly head.

It’s customary during an initial consultation visit to (1) provide introductions, (2) establish a baseline of current activities, and (3) determine desired outcomes for this, as well as future, consulting sessions. Pretty standard stuff, right? Wrong, especially when insecurity is present! Less than twenty minutes into a recent initial consultation session the “Insecure Leader” of the operation voiced their frustration with the process, insisting that introductions and baselines were a waste of time, and that assistance is needed in this/that area (Insecurity?) However, with little/no context provided as to whether or not the “this/that” areas, (Again, insecurity?) were truly where assistance was needed. It left me wondering why I was there if help wasn’t warranted…

What the Insecure Leader is Actually Saying

Insecurity can raise it’s ugly-head in leadership in many ways…

  • There can be the classic bully (I’m the leader and I said you need to do it). There can be the know-it-all (I’ve been there/done that and I know this company/industry/world inside and out)
  • There can be the underperformer (I’m a little behind the 8-ball this month, but it’s the fault of the customers/employees/your visit taking me away from important items/etc.)
  • There’s the spotlight-grabber (Failure is shared by all, but victory is all my doing)
  • There’s the imitator (Just tell me the best-practices going on out there… Pay no attention to our business basics that we fail at)
  • Lastly, there’s tenure (I’ve been here 30+ years…Enough said!)

How to Avoid an Insecure Leader – 3 Tips!

So what should you do when you encounter an Insecure Leader? It’s not a matter of “if” as the saying goes, it’s a matter of “when” you encounter an Insecure Leader. The following are 3 tips to assist you, whether you are managing-up or managing-down with an Insecure Leader:

  • Insecure Leader Tip #1 – Find Pride: Insecure leaders typically share a narcissistic view of the world. What’s not good enough for the goose must be good for the gander. Helping them find pride in themselves and their operation can greatly assist insecurity within the Insecure Leader.
  • Insecure Leader Tip #2 – Celebrate Success: Recognition NOT of how great the Insecure Leader is, but in the potential for greater success is what I’m talking about here. There often is too much coddling of the Insecure Leader and not enough having of tough or difficult conversations. If you’re always telling the Insecure Leader that they’re great, you’re not valuing them, yourself, or your performance potential with them.
  • Insecure Leader Tip #3 – Pull the Plug! I have a friend who is a Psychologist. I asked him once “What do you do when you have a really difficult patient. One where you’ve tried everything and they are making little/no progress. What do you do?” He told me that after he buckles-back and doubles-down to insure that no stone has been left unturned, and once he is satisfied that his efforts have been exhausted, he simply pulls the plug!


In hindsight, I should have taken “Insecure Leader Tip #3 – Pull the Plug!” and ran instantly away from the insecurity present, and more importantly the Insecure Leader. In a consulting capacity, one of my former principal associates shared that he often felt like he wore a bull’s-eye on his back. In the subsequent days since my Insecure Leader encounter, I noticed a warm/burning sensation in my back (figuratively, not physically). I reached back and touched what turned out to be the handle of an ax buried deeply between my shoulder blades. Yep, should have taken Insecure Leader Tip #3!

Sam Palazzolo

PS – Last year I published my fourth book. Titled “Leading at the Tip of the Spear: The Leader” it’s a look into how you can become the best leader possible. You can check-it out here on AMAZON. All proceeds go to The Javelin Institute, a 501(c)(3) whose aim is to assist families who’ve experienced hardship through death, divorce, disease, or drugs.

PPSS – My next book, titled “Leading at the Tip of the Spear: Leadership Strategy” is due out next month. The work is a look into how you can develop your best strategy for yourself/your organization. If you’d like to receive the Introduction please drop me an email at info [at]

Avatar About Sam Palazzolo, Managing Director

Sam Palazzolo is Managing Director at Tip of the Spear Ventures, an agile Venture Capital and Business Advisory Services firm specializing in Mergers & Acquisition, Sales / Business Development & Turnaround Management.