After 20+ years running agencies and managing teams, I’ve witnessed countless professionals walk into toxic work environments simply because they failed to ask the right questions during interviews.
The advertising and digital marketing agency space can be particularly challenging, with unrealistic expectations, poor project management, and demanding work cultures that burn out talented people.
This guide provides the specific questions you need to ask to identify red flags and hold interviewers accountable for their promises. Use these questions to protect yourself from career disasters and find agencies that actually deserve your talent.
Core Business Practice Questions
Do you ever turn away work because it’s not the right fit?
This question reveals everything about an agency’s business philosophy. Greedy agency owners take on every project that walks through the door, regardless of whether their team has the skills or capacity to deliver quality work. This creates a circus environment where teams are constantly scrambling to meet impossible deadlines on projects they’re not equipped to handle.
Watch for interviewers who dodge this question or give vague answers. Quality agencies understand their strengths and regularly decline projects that don’t align with their expertise or values.
How do you manage projects?
Project management systems directly impact your daily quality of life. You need to hear specific names like Trello, Jira, Monday, Asana, or similar modern platforms.
Red flag alert: Run from any agency using homemade systems or spreadsheet-based project management. This indicates leadership that’s too rigid and egotistical to adopt proven solutions. Working in Excel or Google Sheets for project management is a nightmare where you’ll spend half your time searching for information.
If they mention a custom system, dig deeper. Why couldn’t established project management software handle their needs? The answer usually reveals problematic thinking about efficiency and modern business practices.
How do you manage time tracking?
This question exposes how you’ll be benchmarked and what’s expected daily. I’ve started roles only to discover mandatory 9-hour days with minute-by-minute tracking requirements that weren’t disclosed during interviews.
Avoid agencies requiring:
- Punch card systems for knowledge workers
- Facial recognition software (unless you’re in government or cybersecurity)
- Clock-in/clock-out procedures
Quality agencies trust professionals to manage their time. Look for companies using integrated time tracking within their project management system, not separate, cumbersome platforms.
Work Environment and Expectations
What are the expected working hours for team members?
Get specific answers about daily expectations. Agencies vary wildly in their standards, and some have unrealistic demands they prefer to hide until after you’re hired.
If they can’t give you a clear answer, that’s a red flag indicating either unclear standards or demands so unrealistic they don’t want to disclose them upfront.
What level of documentation is required for tasks?
Some agencies require minimal documentation while others demand extensive written explanations for every action. If you struggle with written communication or find detailed documentation tedious, this becomes a quality-of-life issue.
Match your preferences with their requirements. Don’t assume you can change their documentation standards after starting.
How does your team communicate?
Look for modern digital platforms like Microsoft Teams, Slack, or similar tools. Communication should happen on organized digital channels, not through running to offices or hunting down managers.
Poor communication systems indicate poor overall organization and will frustrate you daily.
Professional Development and Support
Do you offer continued education with the role?
Digital marketing evolves constantly. Agencies that don’t invest in team learning fall behind quickly, taking your career development with them. While you should pursue personal learning regardless, agencies that actively support education demonstrate long-term thinking about their team’s growth.
What equipment and expenses are provided?
Remote work has created huge variations in what agencies provide. I’ve seen everything from “bring your own laptop” to full equipment packages including cell phones, internet costs, and premium hardware.
Negotiate for maximum coverage. Internet costs, quality computers, and professional software licenses add up quickly. Getting your agency to cover these expenses directly impacts your take-home income.
Team and Culture Assessment
Am I required to speak with clients directly?
If client interaction isn’t your strength, establish this boundary early. Many talented technical professionals prefer behind-the-scenes work, and quality agencies can accommodate this preference if disclosed upfront.
Was someone previously in this role? Why didn’t it work out?
This question reveals whether they’re replacing someone who was promoted, left for better opportunities, or couldn’t handle unrealistic expectations. The answer tells you whether this role has a track record of success or failure.
How long has your most senior team member been with the company?
High turnover indicates systemic problems. Look for agencies where senior team members have stayed multiple years, demonstrating the company’s ability to retain talent long-term.
In six months, what would you like to see me accomplish?
This exposes whether expectations are realistic. If they expect you to master complex systems and handle advanced responsibilities within six months, ensure you’re prepared for that trajectory or clarify more reasonable timelines.
Process and Systems Deep Dive
How many steps are in your interview process?
Understand what you’re committing to upfront. Some agencies have extensive interview processes that can stretch weeks, while others make quick decisions. Plan accordingly.
How does your team report activity?
Learn whether they use integrated reporting within project management systems or require separate status updates through multiple channels. Efficient reporting systems save time and reduce administrative overhead.
Does this role require managing, hiring, or training people?
Management responsibilities significantly change job scope and stress levels. Ensure these expectations align with your career goals and current skill set.
Salary and Advancement
When is the best time to discuss salary requirements?
Don’t let nerves prevent you from getting full compensation details. You’re working for money, so discussing payment shouldn’t be awkward. Use this question if salary information isn’t clearly provided.
Are there opportunities for advancement or commission?
Understand the growth path and additional earning potential. Agencies with clear advancement opportunities demonstrate they invest in long-term employee development.
Technical and Service Questions
What are your thoughts on [relevant platforms/technologies]?
Ask about their experience with platforms you’ll be working on (Magento, Shopify, WordPress, etc.). Their responses reveal technical competency and whether they understand the tools you’ll be using.
Do you offer analytics as a service?
This question gauges their sophistication in data-driven marketing and whether they invest in comprehensive service offerings.
Is your team US-based or worldwide?
Understanding team distribution helps you prepare for communication across time zones and cultural differences that might affect collaboration.
Documentation and Agreements
Bring Your Own Paperwork If Needed
Never start a role without clear written expectations. If formal job descriptions or agreements don’t exist, create your own document outlining responsibilities, working hours, and performance expectations. Get signatures from hiring managers.
This documentation protects you when leadership tries to change terms after you’ve started. I once used signed paperwork to prevent a CEO from extending agreed-upon 8-hour days to 10-hour requirements.
Implementation Strategy
Use these questions strategically throughout your interview process. Don’t overwhelm interviewers by asking every question in one session, but ensure you get answers to the most important ones before accepting any offer.
Pay attention to how interviewers respond to these questions. Quality agencies will appreciate your thorough approach and provide clear, detailed answers. Companies that dodge questions, provide vague responses, or seem annoyed by your thoroughness are showing you exactly what working there will be like.
Remember: interviews are two-way evaluations. You’re assessing whether they deserve your talent as much as they’re evaluating your fit for their needs. These questions help you make informed decisions that protect your career and sanity.
The best agencies will respect your due diligence and provide transparent answers. The ones that don’t pass this test aren’t worth your time anyway.