Techniques to Command Conversation for Interview Wins

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Today I offer a shrewd interviewing and life leadership mantra. If used with precision, you’ll get anything you want faster. If used carelessly, you will be overbearing and arrogant. 

Sorry, Simon Sinek. While I agree that leaders eat last—when you need to get a job—leaders must go first. 

More specifically, leaders must lean into their leadership and be the first to take a stand in conversations. Savvy readers will also apply this mantra to inform their sales, networking, and life. 

Going first is a highly confident and assertive approach. It may bode better for extroverts.

The approach works because people like to be led. Even leaders like to be led—it’s less taxing on their noggin. 

Seriously. People don’t like to think. Thinking is hard work. Our brain is designed to minimize this energy suck. It’s considerably easier to allow yourself to be told what to think—and, therefore, what to do.

Going first helps you design the executive career you most desire and iron out any mental friction preventing an offer. This is because you control the dialogue’s direction, the conversation’s tone, and precisely what you bring to the table. It makes it easier to give you what you want. 

This approach is akin to assertive interviewing and taking ownership of your lasting impression—but bolder.

A word of caution. 

Make sure you distinguish the meaning of going first from any context around negotiation and compensation. 

Remember, thou shalt not share salary expectations, which means don’t go first when money is in the mix. Some information needs to remain strategically guarded.

Let’s explore the problem, identify solutions, and share examples to help you get started.

The Problem: Waiting For Permission & Giving Up

Occasionally, I’ll get a client who enjoys pontificating about their perfect career scenario. They’ll wax poetic about a magical fairytale Christmas land and idyllic career dreamscapes. But they don’t think it’s possible.

Enter me. 

While I’ve grown to admire ambition and live for the chase—too often, executives start our relationship from a place of exasperation, not motivation. 

They’ve paid their dues and waited for the right opportunity to surface. 

But they’re just not fulfilled—or they just got shit canned and don’t have a choice. So some are hopelessly pointed in the wrong direction, while others are burned out and hopeless. Both states are detrimental.

Sometimes it’s as if they want to use my ‘been-there, seen that’ experience to validate that their pursuit is a fool’s errand. As such, I should exonerate them of their learned helplessness and put their minds to rest. 

While I’d love to oblige them and free their torment, building a rewarding career is not a pipedream, and their perfect executive role probably does exist (but they need to create it).

Folks need to understand that a standout career is not about forever happiness. Instead, it’s more often about the fulfillment that comes from conquering the right amount of hardships. 

I now consider what the stoics call eudaimonia or “good spirit” and what the Swedes call lagom or “not too much, not too little” the closest translation to a successful career.

The problem is that many career-driven hopefuls wait for somebody else to give them permission to be in the right role. They let the rules set by others box them in and don’t even know that they are being confined. Furthermore, they need help determining what actions to take to break down the blockers.

Waiting for circumstances to change what you cannot control will never work. Instead, you must make the first move and chart your own path. 

PS: Read about nothing person Persnickety Milquetoast later. 


The Solution: Become More Self-Reliant

Too often, those with a ‘wait-first’ mentality will come across as weak and subservient, whether they recognize this or not. This may be one reason you have yet to win your next executive leadership position.

Those that aren’t self-reliant, self-assured, and full of self-esteem don’t make strong leaders. 

This is more common when job seekers have weak leverage, are out of work, don’t recognize or cannot articulate their value, or simply just need a damn job to pay the bills. As a result, they often put their prospective employer on a pedestal and must obey their rules to earn a job offer. 

Some may even feel gaslit from the trauma of a previous executive role or disheartened from a rough stint of poorly-matched roles that didn’t work out. 

They no longer trust their leadership and expertise. Instead, they mold their expectations to secure employment. This common gaffe may fly in middle management, but it’s catastrophic at executive levels. As a result, these folks can find themselves in a stagnant or downward career spiral. 

And I get it. Sometimes our work is about the search for daily meaning in our struggle for daily bread. 

But for too many executives rat-racing in a dog-eat-dog capitalist society, the struggle for enough bread and keeping up with the Joneses will dominate and ravage their decision-making. 

I suspect that our frequent comparison to the success of others tricks our brains into fight or flight. 

If societal survival is on the line, even the most successful executives are psychologically programmed to play a subservient role to endure—even though they are not in imminent physical danger. 

My point? 

You must learn to rely on and trust your experience in every scenario, regardless of what negativity has been bestowed on you in the past. This also means taking a stand and holding strong opinions in your line of work. 

Go First, Be Assertive, & Have A Backbone

I don’t get paid to be a squishy co-pilot for my clients. 

No offense to my clay friends Gumby and Pokey, who will mold themselves into anything—but I’d rather have a Steph/Klay or Wayne/Garth relationship with my clients. These power duos stand for something and are not afraid to be themselves. Party on. 

7 years ago, I took a leadership assessment that read, “You scored well in ALMOST every area we look for in leadership. But you scored 2/10 in assertiveness. We won’t hire anyone weaker than a 7 for a role like this.” 

That was a reality check. Now assertiveness is always top of mind.

Maybe this sounds like you (or at least you after you’ve hit a string of bad interviews and your confidence is shaken). 

The more my clients concentrate on being assertive, the better their results—from getting offers to securing bigger negotiations—assertiveness works.

How To Go First When Interviewing

Set the stage by keeping the interviewer focused on the future, not your past. You must win this battle.

Don’t have a laundry list of discovery questions about team dynamics. Save these for after you have an offer. You only get 30-45 minutes with a Chief Executive. Make it count. 

Show them you’ve done your homework and take a stand on the company’s state. Don’t live on the fence. Go all in. 

The team that you’re speaking with should feel impressed that you know your stuff without having to pry it out of you. You must take conversational ownership, drive the interview, and lead the next steps.

For example, you don’t need to tell them, “I looked at your website and studied your product.” Instead, you must show them that you did your research by asking more intelligent questions, asserting your leadership, and being the first to offer valuable consultation. 

You cannot afford to wait for permission to add value or to be served the perfect question. The executive interviewing team cannot spend time wondering how you can be helpful—or you’ve already lost. 

Don’t Use:

“Tell me about the problems you face today. What keeps you up at night?” 

Go First With:

“At this stage, you’re likely figuring out how to move from founder-led revenue to sales-led revenue. How is that going?”

Don’t Use:

“What do your OKRs look like right now?”

Go First With:

“Investors will love to see our team move from unorganized growth to consistent growth to predictable revenue. Let’s talk about how the company’s OKRs reflect that vision.

Don’t Use:

“What are the next steps?”

Go First With:

“I owe you more detail regarding the GTM approach I’ll lead with you. I’m available to discuss this further on Tuesday at 3PST.”

Final Thoughts On Going First

  1. If you discover red flags during the interview process, discuss your concern. 
  2. If you think a company needs a different approach, offer different solutions. 
  3. If you feel you will clash with another executive, say so now. 
  4. If the company doesn’t satisfy your vision for leadership, express your hesitations. 
  5. If first-time founders have burned you in the past, mention it.
  6. If you get shady deceitful crap during the negotiation, walk away.  
  7. If you really are an executive leader—prove it.

Life is too short, and you’re too smart to throttle down your leadership for the sake of round-pegging a square hole. I don’t mean for you to be an obnoxious asshole, but be respectfully assertive, kind, and candid. 

Otherwise, you’re destined to follow someone else’s path, not lead your own.

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