How To Successfully Apply For Top Leadership Roles [Revised For 2019]

Master the art of executive job search.

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Are you an executive who needs to start applying for jobs, but aren't sure where to start? Use these 4 pillars of job search success to guide you.

I’m willing to wager that these four little words haven’t been part of your lexicon for years: Apply For A Job. Why am I so sure?

I’m betting you’ve been a senior leader long enough that the need to search and apply for a job hasn’t been a recent reality for you. Instead, the right opportunities have always found you at the most opportune moments.

But times have changed. The Internet has levelled both the talent search, and job search, playing field — even at the C-level.  

Case in point: Recently, Sheryl Sandberg shared that when she left the government sector and tried to break into tech, a Silicon Valley CEO said to her in an interview:

“I would never hire anyone like you.”

It took Sandberg almost a year to finally land at Google.

So if you, too, are looking to change industries — or are looking to reinvigorate your passion for your profession — give yourself some time to plot your course before you begin applying for jobs.

Philippa Counsell, the Managing Consultant at Arielle Executive, puts it this way:

“Applying for a job at the executive level can be particularly daunting, especially if you’re new to the game.

Philippa recommends dividing your job search strategy into four separate but equal pillars.



Pillar 1: Master Online Job Search.

DISCLAIMER: I started with the one you would resist the most.

I know what you’re thinking: the roles I want won’t be advertised. For the most part, that’s probably true.  But, as incredible as it may sound now, scouring the internet for jobs has a higher purpose: it will clarify your direction.

Even reading about jobs you might never apply for will help you zero in on what you do want.

Successful people change jobs every 3-5 years, so if you’re new to the hunt, it helps to do some genuine soul-searching along the way.

Cindy Hook, ex-CEO of Deloitte Australia, in her six top leadership tips, says that knowing yourself, and understanding what is really important to you, is critical for leading with authenticity.

Hook recommends taking the time to write out core values, even though they might seem obvious. She shares that her personal values revolve around vitality and a life-long commitment to health and well-being.

Within the context of job search, then, when Hook seeks out her next opportunity, she’ll be looking for an employer who shares those values.


Your To-Do List:

  • Keep a running list – what appeals, what doesn’t?
  • Use online search almost like a menu to ensure you’re crystal clear in direction.
  • List your non-negotiables and stick to them.


Additional Benefits:

Being clear on what you want and what unique value you offer to your targeted employers/roles will help you stand out once you actually apply for the job.

Knowing your key message and staying true to your end goal supports your personal brand.


Helpful Hints:

Searching for jobs online will also help you find the people you need to know for the roles you want. Once you’ve honed your list of target roles, create a target list of recruiters and/or search firms whose names keep popping up. This will save you endless time once you begin to reach out, or apply for a job, on your own behalf.


Additional Rules To Live By:

Do: Search online to identify what you do and don’t want to target.

Don’t: Start applying before you’ve done your research.

Do: Use your research to pinpoint recruitment firms advertising desirable roles.

Don’t: Approach a recruiter unless you’re clear on the direction you want to take.

(Related Article: The Smart Way To Deal With Recruiters).



Pillar 2: Befriend Recruiters.

Whether you’re new or a pro at searching and applying for jobs online, executive recruiters can be a frustrating bunch.

I should know; I used to be one. Believe me when I say they are an essential component of your job search strategy.

What most senior candidates don’t know is that many companies outsource their entire executive recruitment and selection process to a single agency.

Yes, executive recruiters often come across as mysteriously elusive. But the reality is they are incredibly busy.

Like it or not, however, they hold the keys to the kingdom when it comes to your search. As in, they wield the opportunities that aren’t being advertised or sourced broadly.


Allow Me To Illustrate:

In Pillar #1, you clarified the direction of your job search journey. You found an executive recruiter who dominates your desired area. You want to reach out.

But first, consider a couple little-known facts about advertised positions:

Once a position is advertised, it’s likely they’ve already sifted through their networks and developed a short list of candidates. You’re already behind in the game. Maybe.

The role you saw online could be a ‘pipeline’ role. This is typical for hard-to-fill positions, including leadership roles. So, it may already have been filled. Or, it could be a typical, but not ‘current’ vacancy.

While it sounds discouraging, fear not.

Roles such as these are a great way to introduce yourself and start building those key relationships. So that next time, you’re the one they pick up the phone and call.

See it as an opportunity to make a connection.


How To Get Started?

Here’s what Philippa has to say:

“Have a ‘hook in’ before you pick up the phone or compose an email. Cold calling or sending your resume with a generic ‘Hi, I’m looking for X at Y salary’ won’t help you cut through the candidate clutter.”

But referrals will. For example:

“David Jones worked with you last year and recommended you to me as an excellent go-to…”

In lieu of a referral, Philippa recommends this two-pronged approach to cold calling:

  1. Always reference a specific role, stating your relevant experience
  2. Be prepared to ‘pitch’ for it. (Refer back to Pillar #1’s bit about knowing yourself.)


Additional Rules To Live By:

Do: Use a role advertised, that matches your skill-set, or a mutual connection, as a way of introducing yourself to a recruiter and starting a conversation.

Don’t: Call a recruiter unprepared, or send a generic email.

Do: Agree upon an action plan on the phone with the recruiter. Should you come in for a meeting? If not, agree to squeeze a phone call in every couple of weeks, and keep to it.

Don’t: Get frustrated online or offline with a recruiter if the role you have applied for is ‘gone’. Use the window of conversation to further your case.

(Related Article: The Smart Way To Deal With Recruiters).



Pillar 3: Use LinkedIn (Yes, You Need It).

Why should you, at your career level, bother with LinkedIn?

First off, because you’ll be in good company. Research shows that more CEOs are on LinkedIn than any other social network.

But here’s the real kicker: If you’re looking for a new opportunity, you need to be on LinkedIn.

Not only to maximize the opportunity of being headhunted, but because the people you meet throughout your job search, and when you actually apply for jobs, will want to see your LinkedIn profile.

The quality or absence of your LinkedIn profile has become a gauge of how serious you are about your career.

To be blunt, it may affect how people perceive you. Furthermore, this point about perception extends to your current colleagues, customers and bosses. Without a great profile, you may creep down in their estimation.


Not A Social Media Fan?

There’s a reason LinkedIn is the most popular social network among CEOs.

Unlike Facebook, no one is posting pictures of their dogs in costumes, or joking about where they went for drinks last night. Also unlike Facebook, you don’t need to hesitate about connecting with someone.

In fact, Philippa believes that LinkedIn will work best for you when you have more connections, not less:

“LinkedIn works on circles of networks, each overlapping and linking with each other. The more people you are connected with, the more visible you will be to be to a wider network as your connections’ connections. Their connections will open you up to a wider and wider circle of people.”

That said, don’t just connect with anyone. Make sure there is mutual benefit, and that the connection serves your greater career goal while offering something back to the other.


Use These 3 Powerful Features:

  • LinkedIn Jobs – This feature allows you to search for jobs that may not be posted on job boards. And it shows you the recruiter’s profile, allowing you to do more thorough detective work, making it easier to reach out.
  • LinkedIn Premium – Similar to being able to board the aeroplane first, this feature allows you to apply for jobs as a ‘Featured Application’, giving you priority over non-Premium members. You’ll also be able to “InMail” recruiters and hiring managers using the LinkedIn messaging app. Even if you’re not yet connected.
  • Groups – Interested in new technology, or looking to explore a new industry? Join a group and meet some new people virtually. Never be afraid to network, ask to connect, or contact people on LinkedIn. This is all expected behaviour for LinkedIn members. But again, be selective. Don’t forget that, after connecting with someone, you need to send a follow-up email to ‘personalise’ the introduction and create a true point of connection.


Final Thoughts About LinkedIn:

Recruiters and hiring managers will be finding your profile via search results, so put your best foot forward. Having a top-notch LinkedIn profile doesn’t serve as a substitute for an exceptional resume. To compete in today’s job search world, you need both.


Additional Rules To Live By:

Do: Review your LinkedIn profile to make sure it looks as it should, and is up to date.

Don’t: Fear reaching out to anyone on LinkedIn. As long as it’s appropriate, and there is a reason for it, LinkedIn is there to be used for exactly this purpose.

Do: Share, like and contribute to topical discussions within your industry or area of expertise.

Don’t: Forget to connect in with existing and new contacts – less isn’t more with LinkedIn. Always follow up with a personal email.

(Related Article: LinkedIn vs Resume: Key Differences You Need To Know About).



Pillar 4: Start Networking (You Know, In Person).

LinkedIn aside, networking in person with other humans is a whole other animal. Especially if you’ve never had to network before as a job seeker. Add to that your desire to make a leap into unknown territory with your career, and suddenly you may find yourself well out of your comfort zone.

But, coming full circle back to Cindy Hook, the unknown is an auspicious place to be. She calls it making yourself future ready:

  • Being “future ready” means taking current skills to the next level.
  • It means having the curiosity and passion to pursue new skills.
  • It means sticking your neck out there and networking face-to-face.

While in-person networking seems as though it happens solely in the moment, there are past and future components to the act as well.



Consider your long-term job search strategy. Your end goal. Purposefully manage your connections.

Be proactive. Reach beyond the people you interact with on a regular basis to stay in touch with those who you don’t normally cross paths with on a routine basis. Once you have close contact, make sure you don’t lose touch.

Identify whom you need to meet and who can appreciate your potential (prospective hiring managers, recruiters and people who can recommend you to these individuals).



Networking works best when it’s about give and take. Think about what else you can offer someone to spark up a conversation.

Be genuinely interested in others. Offer to make introductions, connections, provide advice and offer your unique skills in any way you can.

Stick to any agreements you’ve made in terms of actions and check-in points.



Networking is a long-term project. You may not see results right away, so be persistent. If you don’t have much of a network outside of your immediate circle of colleagues and ex-colleagues, view networking as a career development project that starts now.

It may not find you a job worth applying for this time around, but the key point is to continue it throughout your career to reap the rewards well into the future.


Extra Resources:

Some useful tips for networking outside your industry:

A seminal article for new and advanced networkers:

And for those introverts amongst us who fear it, learn to love it!


Your Checklist:

Do: Start early if reaching out to reinvigorate relationships with old contacts.

Don’t: Let humility or fear of rejection get the better of you – this is business, and in business, you have to ask.

Do: Be consistent, follow up regularly and follow through on actions promised.

Don’t: Give up. Have a game plan, break it down into chunks and keep yourself to it.


In Conclusion:

The more experience you have, the fewer opportunities exist. The math is simple. Middle managers abound in the corporate world, but senior leaders…not so much.

So put your whole self into this effort. It’s your life, after all.

I’ll close with a sprinkle of ancient wisdom and practical advice, from Miguel Ruiz’s book The Four Agreements: A Practical Guide to Personal Freedom.

  1. Be impeccable with your word.
  2. Don’t take anything personally.
  3. Don’t make assumptions.
  4. Always do your best.


– Irene


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