LM - 200 Prompts For Agency Owners

	A	B
1	Funnel Stage	Prompt
2	TOF	What are the non-obvious things you look for in a candidate while recruiting? This can be something on their resume, how they behave, etc.
3	TOF	Did you always want to be an agency owner? If yes, share why. If no, share what made you want to take the leap.
4	TOF	What’s your take on tool bloat? How do you approach equipping your team with the right tools vs overspending?
5	TOF	Is [company] remote, in-person, or hybrid? Justify your choice.
6	TOF	If you weren’t leading [Company], what would you be doing? Why?
7	TOF	What’s one thing that tells you this candidate is going to be a good fit if they do it in the interview process?
8	TOF	Are you still involved in your agency’s Sales process? If yes, how important do you feel it is for that to be the case? If not, when did you know it was time to pull yourself out?
9	TOF	How do you approach monthly, quarterly, or yearly planning as an agency owner? What’s the process or framework that helps accomplish your goals?
10	TOF	What’s your favorite book, podcast, or resource to consume that makes you a better agency owner? Explain it
11	TOF	How did you design your onboarding process? What touchpoints are must-have? What are some non-obvious touchpoints or tactics too many agency owners miss?
12	TOF	What’s one thing that’s an automatic red flag if a candidate does it during the interview process?
13	TOF	Walk through the tech stack you use to grow your agency and service clients. Explain why each tool is needed (and tag each tool on LinkedIn).
14	TOF	What were some of the negative signs or signals you got early on while building your agency? What made you push through anyway?
15	TOF	Pick a company in your space doing [what you do/help do] well. Break down their strategy and what makes them succesful.
16	TOF	Reflect on the last 30 days at [Company]. Pull out 3 “failures” or learnings you want to improve on in the next 30 days.
17	TOF	What was the moment you realized you had something on your hands with [Company]?
18	TOF	Everyone says talent is the lifeblood of agencies. Highlight one thing you wish you knew about finding great talent on Day 1 of your agency.
19	TOF	Why do you love serving your ICP vs others?
20	TOF	What’s the most overrated piece of agency-building advice that you see on your timeline way too often?
21	TOF	What, in your opinion, is the most underrated part of being an agency owner? Working with interesting clients, growing a team, etc. Whatever your answer is, state it and justify it.
22	TOF	Highlight a failed business or venture you once tried. Why’d you start it? How did it get off the ground? What made it fail? What did you learn?
23	TOF	Pick a metric you recently accomplished a milestone for (Headcount, # of customers, etc.). Highlight what you learned about growing [metric] since starting.
24	TOF	What’s one unconventional or “weird” thing you did while building the agency that you know other agency owners didn’t do?
25	TOF	What’s one lead generation mistake you made before that you know not to make now?
26	TOF	Highlight your daily schedule as an agency owner, ideally broken down hour-by-hour. The more specific, the better.
27	TOF	What are 3-5 things you wish you knew about growing an agency BEFORE you started a company in it?
28	TOF	Share a behind-the-scenes story on building your agency that most of your audience doesn’t know.
29	TOF	If you think back to all the ways you grew [Company], what did you think would work well, but didn't?
30	TOF	What's one hobby, passion, or interest you have that people wouldn't know about if they haven't met you? What do you love about it?
31	TOF	Who’s one entrepreneur or mentor you look up to? What have they done that’s so impressive? Why do you admire them?
32	TOF	How do you think about building culture at [Company]? What guides, frameworks, or tips do you use to make and keep the team happy/excited to work?
33	TOF	Reflect on the last 30 days at [Company]. Pull out 3 wins you want to highlight/celebrate (new hires, new logos, new systems, etc.)
34	TOF	What was the scariest moment you had while growing your agency? How did you get over it/improve it?
35	TOF	Talk about how you think through your service offering (what do you offer, what don’t you offer, and why?)
36	TOF	What’s one thing you know other agency owners spend too much time on? Explain it, and justify it.
37	TOF	Why did you start your agency? What was the moment you knew you had to drop everything and focus on this?
38	TOF	Imagine you were talking to yourself on Day 1 of starting [Company]. What would you tell yourself about keeping clients happy and reducing churn that you didn't know back then?
39	TOF	Imagine you’re talking to another agency owner. Highlight 3-5 things you/your Client Success team does to reduce churn/keep clients happy.
40	TOF	Pick your favorite company-building framework, and share how it’s manifested in how you built [Company]?
41	TOF	What’s your favorite interview question to ask a candidate? Why is this question specifically so good?
42	TOF	What is your company’s North Star metric? How do you influence it?
43	TOF	How, if at all, are you using AI at the agency (internal or client-facing)?
44	TOF	Pick 1 “mistake” you made while building [Company]. Reflect on it. Why did you make that choice, what was the result, and what did you learn?
45	TOF	Imagine you were talking to yourself on Day 1 of starting your agency. What would you tell yourself about building your team that you didn’t know back then?
46	TOF	If you think back to all the ways you grew [Company], what worked way better than you initially thought?
47	TOF	What's the least obvious thing you love about leading [Company]?
48	TOF	How can you tell when [process you help with] is “working”? What metrics, signs, or trends should [ICP] look out for?
49	TOF	What Operations or process improvements have you made in the last 30-60 days that made your team operate better/faster? Highlight what makes them so valuable.
50	TOF	What have you learned about acquiring clients since you started your agency that you didn’t know before?
51	TOF	Many people say agencies are hard to scale and tough to run. You obviously run one - so what do you have to say to that?
52	TOF	What have you learned about successfully onboarding a client that you didn’t know before starting [Company]?
53	TOF	What's one leadership book that fundamentally changed how you run your agency? What was the key insight?
54	TOF	Share your most unpopular opinion about agency pricing models. Why do you believe this despite pushback?
55	TOF	What's a routine or habit you've maintained for years that's contributed to your success as an agency owner?
56	TOF	Describe a time when saying "no" to a potential client was the best business decision you ever made.
57	TOF	What's one agency management myth you wish would disappear forever? Why is it harmful?
58	TOF	If you could go back in time and give yourself one piece of team-building advice before starting your agency, what would it be?
59	TOF	What's a common agency workflow that you've completely reimagined at your company? How has it paid off?
60	TOF	Share a mistake you made early in your agency journey that taught you an invaluable lesson.
61	TOF	How do you protect creative thinking time in your schedule as an agency owner? What boundaries have you set?
62	TOF	What's the strangest client request you've ever received, and how did you handle it?
63	TOF	Share your thoughts on the "hustle culture" in agency life. Necessary evil or outdated concept?
64	TOF	What's something about agency ownership that nobody talks about but everyone experiences?
65	TOF	How do you handle the feast-or-famine cycle that many agencies experience? Share your approach to stabilizing cash flow.
66	TOF	What skill do you think is severely underrated for agency owners? Why is it so important?
67	TOF	What's a business "rule" you deliberately break at your agency? Why does breaking this rule work for you?
68	TOF	Share how your agency's core values came to be. Were they intentionally crafted or did they emerge organically?
69	TOF	What's one tool you couldn't run your agency without that isn't the obvious choice? Why is it indispensable?
70	TOF	How has your definition of "success" evolved since starting your agency?
71	TOF	What's a non-industry book, podcast, or resource that's had profound impact on how you approach agency leadership?
72	TOF	Share a time when you had to pivot your agency's direction or offer. What triggered the change and how did you navigate it?
73	TOF	What's your stance on sharing agency financials with your team? Full transparency, partial, or none? Why?
74	TOF	How do you approach personal branding as an agency owner? Share your philosophy on being the face of your company.
75	TOF	Describe a time when following your intuition led to a major win for your agency, despite data suggesting otherwise.
76	TOF	What's one trend you see in our industry that you believe is completely overrated? Why aren't you jumping on board?
77	TOF	Share how your upbringing or background has influenced your approach to running an agency in an unexpected way.
78	TOF	What's one question you ask in every client kickoff meeting that consistently yields valuable insights?
79	TOF	How do you handle creative differences within your team? Share your approach to navigating conflicting visions.
80	TOF	What's a surprising skill from a previous career or hobby that's been unexpectedly valuable in agency ownership?
81	TOF	Share your most controversial opinion about work-life balance for agency owners. Is it achievable or a myth?
82	TOF	How has your agency hiring philosophy evolved over the years? What do you do differently now compared to when you started?
83	TOF	What's one thing you've stopped doing at your agency that drastically improved operations or culture?
84	TOF	Share a behind-the-scenes look at how you structure your typical workday. What non-negotiable blocks protect your productivity?
85	TOF	What's the biggest misconception clients have about working with agencies in your niche? How do you address it?
86	TOF	How do you approach professional development for yourself as an agency owner? Share your learning strategy.
87	TOF	What's an industry "best practice" you've deliberately rejected at your agency? Why did you go against the grain?
88	TOF	Share how you handle the emotional weight of being responsible for your team's livelihoods. What keeps you grounded?
89	TOF	What's one surprising metric you track religiously that other agency owners might overlook?
90	TOF	How do you foster a culture of experimentation at your agency without jeopardizing client results?
91	TOF	What's a personal challenge you've faced that made you a better agency leader? How did it transform your approach?
92	TOF	Share your thoughts on specialization vs. being a full-service agency. Which approach do you believe in and why?
93	TOF	What's one uncomfortable conversation every agency owner needs to have with clients? How do you approach it?
94	TOF	How has your risk tolerance changed throughout your agency ownership journey?
95	TOF	What's a counterintuitive growth strategy that's worked surprisingly well for your agency?
96	TOF	Share how you celebrate wins at your agency—both major milestones and small victories.
97	TOF	What's your approach to handling client expectations during onboarding to prevent scope creep later?
98	TOF	How do you maintain your passion and creativity after years in the industry? What keeps you from burning out?
99	TOF	What's a quality in yourself that initially seemed like a weakness but has proven to be an agency leadership strength?
100	TOF	Share your most unpopular opinion about agency-client relationships. Why do you stand by this perspective?