Should we commit $50k to be the lead sponsor at this industry conference?
Should I respond to their emotionally charged message now or wait until we've both cooled down?
Should I skip lunch to handle this crisis, knowing I've already worked through meals three times this week?
Should I offer this enterprise prospect a 40% discount to close this quarter?
Should I ask the team to work through the weekend to meet this deadline, or push back and risk losing the client?
Should I publicly correct our CEO's factual error in the all-company email?
Is switching vendors worth the 30% cost savings given the 3-month migration timeline?
Should I introduce my new partner to my family at this major holiday gathering?
Should I hire a $15k/month agency for this critical rebrand project?
Should I cancel all my 1:1s this week to personally fix this production outage?
Should I fly to Tokyo for this make-or-break client meeting despite the 20-hour journey?
Should I stay completely offline during my honeymoon or check in daily for emergencies?
Should I agree to a 90-day payment deferral for our biggest customer?
Should I address this team member's performance issues that others have started noticing?
Should I call an emergency all-hands about this competitor's major announcement?
Should I approve upgrading the entire engineering team's hardware for $75k?
Should I deliver this termination on Friday afternoon or wait until Monday morning?
Should I personally fly out to onboard this Fortune 500 client?
Should I pay $5k for overnight shipping to avoid delaying the product launch?
Should I give this harsh but necessary feedback before their important presentation?
Should we cut this $200k annual software contract that only 10% of the team uses?
Should I move across the country for this relationship?
Should the CEO personally call this angry customer threatening to churn?
Should I have this surgery now or delay it until after our Series B closes?
Should I approve this $25k unbudgeted expense for a critical security audit?
Should I share this leaked competitor roadmap with the entire leadership team?
Should I tell them I'm not comfortable at this expensive restaurant they chose?
Should I intervene in this heated Slack debate that's dividing the team, or let them work through the conflict themselves?
Should I authorize double overtime to meet this government contract deadline?
Should I respond to VC partner's email now or wait until after our pivot is complete?
Does this acquisition offer warrant calling an emergency board meeting?
Should we upgrade to Enterprise version at $150k/year for compliance features?
Should I miss my best friend's wedding to close this transformative deal?
Should I organize an expensive team retreat after laying off 20% of staff?
Should I escalate this major customer complaint directly to the board?
Should we break our development freeze to build this feature for our largest client?
Should I engage with this recruiter about a VP role at a competitor?
Should I relocate the team to a hotel for 24/7 availability during this critical launch?
Should we commit $50k to be the lead sponsor at this industry conference?
Should I respond to their emotionally charged message now or wait until we've both cooled down?
Should I skip lunch to handle this crisis, knowing I've already worked through meals three times this week?
Should I offer this enterprise prospect a 40% discount to close this quarter?
Should I ask the team to work through the weekend to meet this deadline, or push back and risk losing the client?
Should I publicly correct our CEO's factual error in the all-company email?
Is switching vendors worth the 30% cost savings given the 3-month migration timeline?
Should I introduce my new partner to my family at this major holiday gathering?
Should I hire a $15k/month agency for this critical rebrand project?
Should I cancel all my 1:1s this week to personally fix this production outage?
Should I fly to Tokyo for this make-or-break client meeting despite the 20-hour journey?
Should I stay completely offline during my honeymoon or check in daily for emergencies?
Should I agree to a 90-day payment deferral for our biggest customer?
Should I address this team member's performance issues that others have started noticing?
Should I call an emergency all-hands about this competitor's major announcement?
Should I approve upgrading the entire engineering team's hardware for $75k?
Should I deliver this termination on Friday afternoon or wait until Monday morning?
Should I personally fly out to onboard this Fortune 500 client?
Should I pay $5k for overnight shipping to avoid delaying the product launch?
Should I give this harsh but necessary feedback before their important presentation?
Should we cut this $200k annual software contract that only 10% of the team uses?
Should I move across the country for this relationship?
Should the CEO personally call this angry customer threatening to churn?
Should I have this surgery now or delay it until after our Series B closes?
Should I approve this $25k unbudgeted expense for a critical security audit?
Should I share this leaked competitor roadmap with the entire leadership team?
Should I tell them I'm not comfortable at this expensive restaurant they chose?
Should I intervene in this heated Slack debate that's dividing the team, or let them work through the conflict themselves?
Should I authorize double overtime to meet this government contract deadline?
Should I respond to VC partner's email now or wait until after our pivot is complete?
Does this acquisition offer warrant calling an emergency board meeting?
Should we upgrade to Enterprise version at $150k/year for compliance features?
Should I miss my best friend's wedding to close this transformative deal?
Should I organize an expensive team retreat after laying off 20% of staff?
Should I escalate this major customer complaint directly to the board?
Should we break our development freeze to build this feature for our largest client?
Should I engage with this recruiter about a VP role at a competitor?
Should I relocate the team to a hotel for 24/7 availability during this critical launch?