What Is This?
This post/page is a compiled, concise list of lessons I’ve learned over the course of my career. I’ll regularly come back & update this to a living, ever changing, document.
Questions To Ask
In 1, 2, & 5 years what would make this successful or unsuccessful? i.e. What things would make you either look back and be happy you hired me or regret hiring me?
This can highlight both the unspoken deliverables and the regrets can be a sign of past lessons learned (or what employees have done in the past to upset the employer/boss/interviewer).
What are the key deliverables?
A company that posts a job without clear deliverables is making questionable decisions. The easiest example of this is simply the applicant requirements in the job posting. The ideal is if the employer has KPI’s already defined such as “build # of relationships with potential customers” or “generate $ in new income” or “respond to website inquiries within 2 business days”.
What responsibilities would I have? I personally am not the person to “live & die by the job description”, just because something is not listed as my responsibility doesn’t mean I won’t do it.
This helps you understand the minimum expectations or if there is no responsibilities that can be a sign of an ill-defined job.
Can we make a list of milestones/achievements? Those can be financial (i.e. write $1m in new business), they can be educational (complete the CAIB or CIP), or they could be task based (i.e. rewrite our u/w manual, complete a coverage review of wordings, or develop a technology plan).
Milestones and achievements, even if just the first 30/60/90 days, help you as an employee know you are on-track of off and it helps the employer know in the first 3-month review window if they’ve made the right decision.
Do you have a growth/development plan? If an employee shows interest in progression how do you support and develop that employee?
No growth plan or “we’ve never really thought about it” is a concern. While on the positive side “in every annual review we discuss where the employee wishes to be in 1-year and make a plan for achieving that”.
Who will be my direct boss?
Sadly, I’ve found this needs to be outlined. In almost every position I’ve had there has been 2+ direct bosses and often conflicting priorities/requirements. For simple math, how would 2 or more bosses work in a performance review; is it a panel review? or is 1 boss left unheard? or does the employee have multiple performance reviews?
What are red flags for you when interviewing new staff?
Again, this can shed light on past unacceptable behaviors/actions of employees. On the flip side, no red flags can be a sign of an unwillingness to share or a disorganized interviewer. It’s really easy to Google this for new interviewers (and you should in order to prepare for interviewing people the first few times).
What is the long-term/ideal plan for me as an employee?
This needs to fit with your plan. If you have a family and want long-term, stable employment then you hope that’s the plan. On the flip side if the answer is “we want you to build a rocket to fly us to the moon and become our CEO” then they may have unreasonable expectations.
Do you perform regular/annual reviews?
Every job I’ve ever had has committed to semi-annual reviews but not one has done that. In fact I think I’ve had <5 annual reviews in my life.
What title/position are you hiring for?
Honestly, as an employer you need to get this sorted out internally before posting a job. If it’s “we have a problem and need you to solve it” then the question becomes “OK, when I’m successful in my job and solve your problem what happens to me? Am I made redundant?”
Do you have corporate training/development/mentorship?
If an employee shows initiative, drive, passion, or enthusiasm but the organization doesn’t support and grow that, they’re probably not supporting staff in other ways. That being said, there needs to be plans for “the receptionist at the tire company that wants to become a rocket scientist” since this is outside the scope of the core business.
What challenges are your staff currently facing?
An inability to answer this can be a sign of disconnect between management and staff. That being said, a long list of challenges/frustrations can be a sign you’ll experience those same problems without any resolution.
What challenges are your business facing?
An inability to answer this can be a lack of understanding of the business/market. If a business faces 0 challenges then they should be wildly successful, wildly profitable, and living in a utopia. Granted the answer to this could be proprietary information so a good interviewer may decline to answer this question or provide a limited response.
Who are your competitors?
You, as an applicant should already know this. Every organization has competitors even if it’s “lack of discretionary spending money” or “a university in Spain that provides the same course content and nicer weather”.
Can you share with me any unique business strategies, marketing, competitive advantages, or products planned?
You can’t expect a potential employer to share proprietary information before you sign an employment contract and/or NDA. But, every employee in an organization should be able to tell you what makes the organization unique and competitive. If this information isn’t available there could be a lack of internal communications and team-building.
You also want to see excitement for new products/strategies and true belief in the competitive advantage(s).
Can you share with me any changes the business is currently facing or going to face?
Every organization is always changing. The fact the org is interviewing and hiring is a current change. An interviewer is a representative face of the org so they need to be aware of the current business climate.
Do you normally promote within or hire from outside?
Promoting from within builds up existing staff and is less risk (promoting a known employee rather than a new hire). But, hiring externally can get a better candidate than only looking internally and can be a source of new ideas, new energy, and new perspectives.
Do you have a regular team/function meetings? What sort of things are discussed?
This could be “all Vancouver staff” meetings or could be “all server admins”. The key is that there is regular 2-way conversations between the people doing work and the people managing them.
Can you please take me through your customer/data journey from start to finish?
Every employee needs to know at least the basic process a customer or stakeholder goes through from start to end. Even if its just high-level, ultimately customers/stakeholders are the ones paying your salary so you need to understand them and their pain points to ensure you continue earning a salary.
What key reporting do you run/analyze?
If you’re not aware of the current state of your business and how it compares to historic performance, are you really running a business? If those reports are not easy to access then the org is probably devoting far too much energy to reporting and data, it should be self-serve and near-real-time.
Can I see those reports? Maybe with numbers scrubbed if you don’t want to share.
The outcome of this question is a toss up. On the one hand if the interviewer shares extremely confidential financial information that could be a sign of serious security concerns and how they might treat your own, personal, sensitive information. On the other hand if interview expresses anger or frustration at you for even asking then the organization might be too inflexible or too secretive.
What discussions/thoughts are happening around any special projects? And what requirements are there? Regulator approval? Investor Approval?
It’s challenging when a new employee joins the org with an existing job description and new/special projects or dumped on the “most junior person”. You want to see clear, concise plans and understanding of current workload in new/special projects.
What is the maximum size of meetings for your org?
In these days of COVID it’s not unusual, in large orgs, to have meetings of 100+ people. At that point I think the topic of the meeting could easily be an email or pre-recorded video of “the presidents message”. If every person in a meeting isn’t going to contribute then it can be asynchronous and take up as little time as possible.
Has your org ever fired multiple people in the same video call or in the same room?
Obviously being let go or laid off from employment is a difficult time for any employee. As such, the employee should be treated with compassion, respect, and discretion; the complete opposite of public firings/layoffs. And if managers are managing so many staff that they can’t devote that personal care to each employee then they are obviously stretched too thin or the the org structure needs improvement.
Why did the last person leave this role?
Granted this is personal and the interviewer likely won’t be able to answer. But answering “oh, that idiot was fired for not generating enough sales” speaks volumes about the org and interviewer.
Take me through the financial lifecycle. Let’s work backwards from a dollar of salary and the accounting system and donors & government funding.
Bottom line the accounting needs to be sound, the accounting department needs to be on top of things, and senior leadership needs to be aware of the current financial position. You’d be amazed how many (large and small) organizations I’ve see where accounting is often off by $1-$10,000. Or, its not uncommon for a senior leader not to know the current runway if all income suddenly dries up.
Take me through the income, grant, or fundraising lifecycle from finding a potential grant/customer, researching market/eligibility, writing the marketing/application, applying, addressing followup questions, accounting, etc.
Who does what and is there any gaps in the process from product to customer to sales.
Give me your standard elevator pitch, investor pitch, customer pitch, or donor pitch for your org.
If the person interviewing you is at a party, what do they say the company does? Do they say it with positivity and enthusiasm or burnout?
What metrics will you use in my 1, 6, and 12 month performance reviews?
You really want to know what makes a candidate [un]successful to be the best employee you can.
Insurance Specific Questions
What tools do you have to assist underwriters in selecting the right rates to charge?
Do you have a regular underwriting meeting? What sort of things are discussed?
Tell me about your document issuance process.
Signs To Definitely Not Take a Job
- Arrives late for meetings.
- Once in a while is fine. Valid reasons for being late is fine. Scheduling an interview at 10am but not holding the interview until 11:30am is disrespectful and a waste of the applicants time. Imagine if you hired that person and they showed up 1.5hr late on their first day or every day. Treat applicants/employees as you wish to be treated.
- Using a phone while in an interview.
- Believe it or not, I had a VP in an interview who spent the entire time on his cell phone. I’m not sure why he was even in the meeting if he wasn’t listening, engaging, or paying attention. Was he there simply because he didn’t trust his managers?
- Again, imagine the applicant spent the entire interview on their phone.
- Focused solely on numbers/sales.
- Yes numbers, KPIs, and income are extremely important. But, if a boss has to choose between “winning that big account” or “employee being on time for their own wedding” the boss better choose the right one.
- Staff are hired to solve problems and deliver solutions/results. Income/numbers are one result of those things but reduced risk, improved moral, reduced turnover, and happier customers are also important results of the work staff do.
- Employees not smiling when you arrive for the interview
- If the current staff aren’t happy there’s a good chance you won’t be either.
- 1-line email replies
- Many emails don’t require more than 1 line responses and that’s OK. But if you ask a few questions that require detailed answers and the response is “yes to all of those” then it might be a sign your new boss doesn’t read emails, is unable to delegate, or is stretched too thin.
- Does not respond directly to questions & concerns in emails
- Believe it or not I’ve had potential bosses answer the positive questions in an email and ignore the negatives. If they pick & choose what to answer in the hiring process they’ll likely do the same in your day-to-day work.
- Speaks negatively of existing or past employees
- Another thing I’ve had [potential] bosses do and it’s not a good sign. As a leader, if you don’t have something nice to say…
- As a rule of thumb, staff should only ever complain/vent/speak-negatively to those in equal or greater positions in the company. And certainly never to applicants. It’s impossible to know who is in what social circles or the background of why an employee left. When an employee leaves a company for any reason they’re gone and the org/boss needs to just move on.
- Speaks more of remuneration than challenges/responsibilities/function.
- I’ve found this is often a sign the challenges/responsibilities outweigh the remuneration so the interviewer is focusing on the remuneration to sell you on the job and cloud your judgement.