Master Your Executive Level Job Search
Updated: Mar 14
This seven-section guide offers proven tips to help you navigate the executive level job search process and it will be invaluable at any time in your career.
As a trusted advisor to executive leadership teams and boards of directors with more than 25 years of experience in retained executive search, I feel privileged to have helped many companies achieve key strategic and operational business goals & objectives through the talented leaders my teams and I have brought to their companies. I have learned a lot along the way on job searching and interviewing best practices, and have gained a unique perspective on how candidates can secure a great executive level job. In the pages that follow are some of my favorite tips separated into 7 practical sections.
1. Starting A Job Search
Before submitting any resumes or starting to network, a recommended starting place is to write an outline in one column describing what you want your next job to look like in terms of:
Target industries, companies, job titles, and areas of responsibility
Organizational cultures you work best in
The type of environment you want to come into: stable or a turnaround, a build or maintain role, market leader or elsewhere in the pack etc.
The skills, strengths, traits, drivers & leadership competencies you want to utilize
Pause to make sure the strengths & skills you want to leverage align with the jobs that interest you
In addition, many individuals find it helpful to write in a second column, what you do not want in your next job, utilizing the same categories above
Try to lay out where you want to be in 5, 10 and 15 years from now, With each opportunity you explore, ask yourself how it prepares you for that long-term plan.
After thinking carefully about the above areas, take time to create a dynamic resume and cover letter, and also polish off your LinkedIn profile.
2. Resume, Cover Letter, and LinkedIn Profile
Your Resume - Many executives we speak with have not updated a resume in years, including a percentage who have been at one company their whole career, so it can often feel overwhelming to put together a current resume. The following tips will help you create a winning resume...
Is customized to specific opportunities, highlighting aspects of your career that are most relevant
Includes a career/executive summary at the top of the resume, with key accomplishments
Includes skills, competencies and strengths (SCS) below the career/executive summary
Goes beyond traditional, overused corporate jargon when listing the SCS
Includes a section that lists some of the strategic and tactical deliverables you can achieve for your next employer based off of your key accomplishments and SCS
Demonstrates results achieved (results/outcomes-focused)
Presents quantitative information that potential employers can connect with
3 out of every 4 resume bullets should include quantitative data
Includes a phrase below each of your employers that describes them - make them sizzle because it shows how you will be enthusiastic for that new employer too
Uses a font size that is clearly readable – 11 point or slightly larger is ideal. 10 point is okay.
Is succinct in whatever information is presented (try for a 3 page max)
Excites the reader and leaves them wanting to learn more about you
Talks about prior employers in a positive way
Does not include a photo, but does include a link to your LinkedIn profile
Has only one font, maintains balance, keeps formatting consistent, and steers clear of acronyms, abbreviations and contractions (unless they are previously defined in the resume).
Has at least 3 bullets for each job entry, and ideally only 3 if the job was held under 1 year
Your Cover Letter - If a cover letter is requested, it should be addressed to a specific person, indicate a mutual connection if there is one, state why you are reaching out, and include a ½ page career/executive summary describing the background you bring to a future employer and also what you can do for that company. Some additional quick tips:
State how your capabilities align with (a) the deliverables for the position (b) that company’s mission statement and values stated on the job description or company website
Share one thing you have learned through your career that will benefit a future employer - humility goes a long way with most companies
Your LinkedIn Profile - Whether an emerging leader or at the executive level, a LinkedIn profile is an important aspect of a job seeker’s brand. Whereas you may have multiple resumes, you should only have one LinkedIn profile, so make it as solid as possible, and as universal as possible. A good LinkedIn profile:
Is up to date
Provides a nice overview of your entire career, and it provide viewers with a good idea of your background and what you bring to their company. (It need not have all the specific job details that a resume has)
Has links to any articles or presentations you have authored or where you were a source
Includes a recent in-focus photo (ideally a headshot), is either business casual or business formal, and is one where you are looking into the camera vs away from it.
3. Your Outreach & Networking
Once you have a great resume, cover letter and LinkedIn profile, it’s time to start your outreach. You might be surprised to learn that for over 80% of executive level candidates, a typical job search involves casually contacting a handful of colleagues and a few executive recruiters in their network, and sending resumes in response to jobs posted on LinkedIn or other job boards. While a few executives might make 3 calls and obtain a job offer before the week is over, I would like to highlight a more effective and comprehensive approach, especially since most job seekers never have the 3-call success and because most of the best jobs never make it onto a job board. Some recommended actions are below…
It is a numbers game, so I encourage you generate a list of 30-50 people you can connect with
Categorize your network into 3 tiers, based on the closeness to that connection
Ask for the most help from your tier one connections. Tell them what you are looking for and ask them if they know of pertinent opportunities and for referrals in their network
Reach out to the board members and leaders of key industry associations that are relevant for the positions you are interested in - let them know you are in a job search. They may know of opportunities, or they may be able to connect you with others who do.
Let each person you connect with know the level of confidentiality of your job search
Connect with 15+ executive recruiters, including partners at the largest firms (Heidrick, Spencer Stuart, Korn Ferry, Russell Reynolds and Egon Zhender. Those firms are executing the largest number of concurrent assignments. You can go to the company websites to filter consultants by industry and functional specialties, and you will likely find their emails.
Pick up to 10 additional executive recruiters from boutique firms, and include them in your outreach as well, such as our firm, J. Tedesco & Associates.
You may find it valuable to join bluesteps.com which can link you up with search firms
Leverage LinkedIn by connecting with senior level colleagues, including ideally who your boss would be. For example, if you are interested in a VP Operations role, you might try reaching out to the COO of that company (regardless of whether or not that have an open posting for such a position).
- Introduce yourself and express interest in sharing your resume
- Often, if a search firm is leading the assignment, you will get directed right to the partner at the search firm, which skips a couple steps in the process
Create a system for tracking your outreach. I recommend a CRM (such as ACT) vs using a spreadsheet. It will help you know when you need to follow up again.
One of my favorite tips:
Keep in mind that executive search consultants are typically reaching out to top notch candidates who are currently employed at the best companies in a particular industry, and trying to recruit those individuals to another company. Often however, that individual is happy and not interested in switching jobs. Contact those individuals! There is a good chance that they will be able to tell you who is hiring (I am sure they received at least one executive recruiter call within the last 1-2 weeks).
4. Interview Prep
Congratulations – you have been invited to interview! Here are some recommended actions:
Review the job description very closely.
- Read each bullet and think about questions that could be asked to address each bullet.
- Write answers to those questions and rehearse responses in front of a mirror
Google “common interview questions” and prepare responses to them
Review all the company literature you can, such as corporate filings, sustainability reports, press releases etc, review the company website thoroughly and research the backgrounds of the individuals you will interview with (you might even find videos of presentations they have made
Write down the names and titles of key leaders in the company, so you can reference them
Do some mock interviews with a colleague or family member, and practice your response in front of a mirror, so you can see how you present
Ask yourself and others in your trusted network what questions they would ask if interviewing for this position and prepare & rehearse responses.
As you prep, keep in mind that, in general, initial interview responses should be under 2 minutes, to allow for follow up/probing questions, but if you can answer a question in less than 30 seconds, by all means do it.
Write out and then bring questions with you to the interview that demonstrate your knowledge in specific areas as well as your knowledge of best practices for that position or industry.
Beyond the questions you have written down for the interviewers, I highly recommend writing out outlines for topics you expect will be addressed during the interviews.
- For questions that address a process improvement, department redesign or other major initiatives, list the pain point/problem/issue, what was the process you went through, including the timelines and milestones, the obstacles you overcame, the result, how results were measured, the benefit back to the company and also something you learned through that process.
- A hot topic is diversity, equity and inclusion, so be prepared to address this topic in detail
5. The Interviews
Bring it!…. Dress for the interview, show up early, be polite to every person you interface with and allow the company interviewer/s to drive the interview. This holds true for phone, video or in person interviews.
Use a time piece to manage your response time to questions and to the allotted interview time
As mentioned in the interview prep section. if you can answer a question in less than 30 or 60 seconds, great! If it takes 2 minutes, that is fine too. If you push 5+ minutes you will lose your audience and not allow time for probing questions.
For video interviews, a colleague who is a successful news anchor in Chicago recommends having your camera raised up to eye level (a laptop on books works well) and have a background that does not distract or create a backlit situation.
Bring/Have a portfolio that includes the names, titles and key background elements of people you will be interviewing with, along with some stats about that company – look for ways to work those things into your conversations. Also in your portfolio, write out:
- Outlines of key processes you have improved
- Changes you have led
- Businesses you have improved
- Teams you have restructured
- Strengths and how they have contributed value
- Weaknesses and how you have strengthened them
- Technologies you have leveraged (and perhaps implemented)
- How you manage a remote workforce, and be ready to discuss your approaches
to remote work
After your interviews, send thank you emails to each person you met with or to the group, customized to each conversation. The interview coordinator or search firm can get those emails for you.
Some Favorite Tips:
As mentioned in the interview prep section, when asked a question, answer by sharing the situation/problem, the process you went through to address the problem, including a timeline, the obstacles you had to overcome, the result, and then the benefit back to the company. You might also include any lessons learned along the way.
Search the internet or ask colleagues for materials that outline best practices in areas that you expect will be addressed during the interview. Be prepared to integrate examples that follow that best practice approach.
Look for opportunities on select interview questions to flip it back at the interviewer. After you have answered the question, ask them how your response aligns with issues they are dealing with – if you have done your homework, you will know it aligns well and will open up the dialogue to be more conversational. Just do not do this on the first 3 questions you are asked.
Some Final Thoughts on Interviewing: Interviewing is a skill that can be practiced and improved upon. Be upbeat and authentic in your delivery of information. People want to hire individuals who they can see themselves working with, so steer clear of any topics that might be polarizing or off-putting to your audience. You will do great!
6. The Offer & Negotiation
You may have already been asked about your targeted compensation range, and so you knew an offer was likely. And now it happens, Congratulations! You have received an offer – now what? First of all, thank the company for the offer and let them know you will review it and circle back with your impressions and likely some questions. If the initial “offer” communication was purely around salary and annual bonus, ask for other pieces of the offer right away, such as benefits, long term incentive compensation details and other standard perks of the job. As you start to process the information presented to you, keep in mind that, depending on the company, there maybe a lot of areas you can negotiate on. Here are many of them:
Target annual cash bonus
Long term incentive bonus
Sign on bonus
Moving cash and moving allowance
Temporary housing expenses for x months and a housing subsidy
A special pay line addition for living in a higher cost of living area
Business clubs, airline clubs, country clubs, and gyms
Reimbursement for education, certification, and industry association membership
Travel fund for trips for you and your family to unite until a family move occurs
Negotiate for bonuses to be paid at the 6-12 month mark if it cannot be paid upfront.
Severance package (now is the best time to negotiate for that)
Since a growing list of states cannot ask what you currently make (due to laws governing equal pay), leverage a website like salary.com, which can help you see how your role is compensated at other companies AND how other people at your same level are compensated within that target company.
There is a lot to say about how to negotiate – some of the basics include being confident, but respectful, having data or an explanation to back up your requests, know that a position typically falls within a pay band and is structured around internal equity, so there will be limits on salary. Be creative with the other levers if salary is a sticking point. Stay optimistic.
The greatest value that references provide is that they give insights to your future employer about how you work best, and how to best manage, support and develop you to ensure your immediate impact and long-term success in the company. Here are some recommendations about references:
Provide at least 4 references that cover roles you have had throughout your career.
Ideally, you will want to provide 5-7 references that include both long-term and recent relationships, and that can provide a 360 degree view about the candidate (boss, peer, subordinate, vendor, consultant, other executives, company CEO, board members and industry association leader, regulator etc).
Even if your search is confidential from your current employer, you should ideally find someone you can trust at your current employer (especially if you have been there for more that 3 years) who can provide information about how you have performed in that company
Make sure references are prepped for the conversation and share the attributes about you that you know are important in the eyes of your future employer.
I hope you find the above guide valuable! There is a lot more that can be shared on each one of the above categories, so please reach out to me directly with any questions via email: JLT@tedescoassociates.com
Wishing you much continued success in your career,
Jonathan Tedesco is the Managing Director of J. Tedesco & Associates, a nationally recognized, retained executive search and talent advisory services firm, founded in 1998, with offices in San Diego and the Midwest. He can be reached via email at: JLT@tedescoassociates.com